Breaking Down Walls of Insecurity

by Arianna

Age: 39
Race/ethnicity: White
Location: Canada
Highest education received: Some college (not currently in college)
Occupation: Technical
Religious affiliation: Conservative/Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

Breaking Down Walls of Insecurity

How long ago did this hookup happen? 3 Years

How would you best classify this hookup? Fuck buddies

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 met my partner on a hookup dating site, because I had become so jaded from trying to date “normally” through another site.  Despite not asking for hookups or sexual encounters, any  messages I received were always sexually driven, contained innuendos, or within hours of starting to chat via text and phone, I’d be sent photos of genitals. I decided that ultimately, we were all looking for sex, and that I would be better off going on a site tailored to just that, thereby allowing me to seek and find *exactly* what I was looking for. In this particular stage of my life I was also in a self-punishment phase I recognize now as potentially harmful, but at the time I was intent on breaking past some barriers I had towards sex, men, and intimacy.

I began messaging one man and we exchanged info. He was an accredited professional in my city and had several verifiable types of content online so that I could feel secure with him. I very much at this time did my research when it came to online dating- tracing IP addresses, finding anything I could about them and being well-informed. Initially we ended up only talking via email for almost 6 months as I temporarily ended up in a short term relationship where it would not be appropriate to step outside of it to continue this. But we resumed as soon as that ended, and our frenetic kind of getting to know each other amped up to the point where we decided we must meet.

We decided to give each other an in-person look-see in a public place. I viewed him having a coffee at the coffee shop below my office, without him knowing who I was. I was able to locate him from his red tie, and observe his appearance. Later that day, I arranged for him to check me out in a drug store as I shopped for cosmetics. In my peripheral vision I could see him checking me out from afar, and it was a turn on.

Following this, we both confirmed we were physically attracted to one another and an encounter could be possible.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was extensive planning to our hookup. I was, as previously mentioned, very much in a place where I wanted to push past some boundaries of my own, find my limits and fears and break past those, but in a somewhat safe manner. (For me, this meant the background check etc).

The plan was that we would meet and fuck immediately, but it was to be involving a lot of excitement and build-up. I took a key to my door of my apartment and placed it on a ledge outside an office building near where he was attending a corporate event. I texted him the location of this key, and he retrieved it. For more than a week, he had a key to my place, but no address. The sexual tension and anticipation was very necessary for me, and fed a lifetime addiction I have to adrenaline rushes, excitement and the unknown as far as adventures go. He told me that finding the key there as I had promised made him too very hot, and that he found the experience very pleasing too.

Our banter continued, and we discussed at length our turn-ons and details that added to the potential hookup. When I finally was to text him my address, I was to pick an evening, and he wanted me to be waiting naked in my bed, doggy style, and we would fuck right on the spot. For him, having been betrayed in his marriage, having a partner who would not barrage him with commitment, and all the confinements of dating was big for him. For me, it was merely about pushing my limitations of fear and being totally free in the sexual arena.

I was extremely nervous, but for the hour or so after I sent him the address and knew he was on my way, I was also incredibly sexually charged up and turned on. I was fully testing my limits of everything I knew- and it was so hot to me. When I heard the key in the door, I was shaking, but naked and very, very wet.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I had chosen to go one step further with myself sensory-wise and blindfolded myself. I was 100% completely vulnerable and trusting that he wasn’t wielding a machete and going to kill me. This vulnerability only added to my sexual excitement. I felt him enter my room, and upon seeing me waiting on the bed, he sucked in his breath and exhaled saying “yes, yes.” This was exactly what he was looking for, and judging from my eager wetness, it was also what I craved.

He spent a few moments toying with me, playing with me, gently touching my body, prolonging our excitement. I could feel his massive hard on touching me in various places as he navigated around the bed, consensually exploiting my vulnerability. He licked me, pushed a finger in, and I cannot recall a more hot and exciting sexual encounter than this was proving to be.  When he disrobed and positioned himself behind me, I was almost bursting with anticipation, and our breathing was over the top. He entered me, and it was an incredible fuck, to both my hungry body and my equally hungry mind. He fucked me like a champion, and pulled out and came all over my back, hotly, with his huge load. Feeling this total stranger who felt strangely familiar to me panting in my ear, collapsing on top of me was the completion of a highly memorable sexual, animalistic act that I totally controlled and orchestrated myself.

What made this man a perfect candidate to what has ended up being a consensual, long term hookup is the fact that he didn’t just zip up and leave. Afterwards, we bared our souls and talked for almost an hour, revealing other vulnerabilities we each had about past relationships, how exhilarating we had found this, and just getting to know each other more as friends.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? The first time we fucked we used a condom and I was on the nuvaring. We had both produced medical testing during our pre-sex chats and no further discussion was made. Over time we eliminated using condoms, as I believe he was fixed from his marriage from having any more kids. To be frank it’s simply not come up.

What were your REASONS for having this hookup? I orchestrated this to help me move past what had happened previously to me in a very very toxic and bad relationship. I had felt I’d reached a crossroads where my life could either go in a direction of almost agoraphobic behaviours towards men and dating, or I could force myself to feel the fear I was so afraid of, and move past it.

Were alcohol or drugs involved? If so, how much? I smoked a big joint prior to him arriving and continue to do so whenever we hook up now. It adds to my being relaxed and ability to be totally uninhibited towards him.

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 feel this is one of the best things I’ve ever done – in large part because we continue to have each other in our lives today, 3+ years later. I end it whenever I enter into a long term relationship with someone else, sometimes for almost a year. After that ended, I tentatively reached out to see if he was still available to me for sex. I have no desire to be promiscuous fucking other strangers if I can reconnect with this man, because naturally our sex is off the charts after doing it so many times since that first hot encounter. Many of our subsequent encounters mimic this same setup – he likes me to be waiting naked, ready in a variety of poses.

To whom did you talk about the hookup? How did they react? I have a number of close friends (girlfriends) and most of them know the situation. As most of them are married with kids, I have always been the one they live vicariously through anyways, and most loved hearing about this story and considered me to be quite brave for going through with such a scenario. Some expressed concern at the safety element, but they also know I am a worldly, intelligent person who would have performed the requisite due diligence. I am sure some judged me inside, but never voiced it, based on a few questions I was asked after the fact.

Was this a consensual and/or wanted experience for you? For your partner? It was very much a mutually consensual experience for both of us, and I personally very much wanted it.

Do you regret this hookup? If so, why? I do not in any way regret this hookup.

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? This hookup has been hugely beneficial for my sexual evolution as a person. It allowed me to grow very comfortable with my naked body, particularly in the sexual arena, and removed many inhibitions I had. I also learned many new areas of turn-ons for both me and a man, and we also had extremely enjoyable anal sex on a number of occasions because of my trust for this man. I will forever think of him fondly, even if the relationship I am in now means I won’t be with him ever again. It is nice to know that a hookup can be positive, and can provide considerable benefit if approached with one’s eyes wide open as was the case here.

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 or anything else? A few times during the years I have known this man, I have at times wondered if there was ever any possibility of us being friends outside the bedroom since we have so much common ground sexually. But I am also adult enough to realize that part of why we’ve been able to meet on such a mutually sensual level is because we stripped away any other “normal” obligations and made this just about pure sex. From our pillow talk I do see that we would make good friends who would probably enjoy each other’s company, and ironically a dating site I used afterwards matched both of us up as a match. Funny!

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