Sex with a Spy

by Jess

What’s your gender? Woman
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Consultant
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

sex with a spy

How long ago did this hookup happen? 5 months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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

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? Gorgeous mixed man, way out of my league, athletic build, nice arms, well-dressed, great ass. Met him at my hotel during a work trip abroad, just a few hours after I landed. I was talking to a group of Americans and initially found him detached/disinterested (and sort of obnoxious, truth be told). After speaking to him for a bit, went to my room, passed out, and didn’t think anything more of it. A few days later, I was having dinner with colleagues and he was meeting a buddy he had deployed with at the hotel, near where we were sitting. For some reason, still unclear why, we came up to one another to say hi and ended up engrossed in a conversion for a good 15 minutes. I didn’t want to ask for his number in front of my colleagues, and I didn’t get a chance to ask for his number that night. Later, a colleague of mine told me that homeboy was most likely a spook posing as military.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About a week and a half later, I was having beers with colleagues near the pool area of the hotel and noticed him inside, having dinner. One of my colleagues, who had met him at a FOB (Forward Operating Base) in a different part of the world, noticed him and invited him over. He sat down with us and one by one, my colleagues dropped off until it was just us. We talked until 3, maybe 4am, and exchanged numbers. We had an insane amount in common, for being multi-lingual to having similar obscure tastes in movies to shared values blah blah blah. I was insanely attracted to him and couldn’t go to bed that night, freaking out about the fact that I would probably end up cheating on my boyfriend.

The next day we texted back and forth, and I invited him to my hotel room for drinks. He is extremely well-spoken, and his well-written texts added to the attraction (I know, I know). That evening he showed up at my door, looking hot as fuck, with some prosecco. We talked for a few hours, and the conversation turned to martial arts, which we have both done to varying degrees. I ended up showing him some grappling moves (demonstrated a pin on him), and found the experience of laying on his muscular chest a huge turn on. He also didn’t know basic escapes, which was cute since he’s deployed to these crazy places.

As we got up, he pulled me in for a kiss. Absurdly hot. That night we took each other’s clothes off (fuck that BODY of his) but didn’t have sex.

The following day, we went for a hike and talked – made out some more that evening in my hotel.

A few days later, I had to go to a neighboring country for a conference, during which we texted and talked almost constantly. The night I got back, I had him come to my hotel room at midnight and practically jumped him when he showed up at my door.

After a few drinks, we tried to have sex for the first time, but he stopped before entering me. Despite being nearly 12 years older and having had a multitude of partners, he felt that it was rushed. We made out some more, and fell asleep in each other’s arms. I found it kind of cute that he didn’t want to rush it, for whatever reason.

The next morning, after lazily making out, he asked if I wanted to have sex (uh, yes?). He put a condom on his huge (black!) cock and entered me.

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? We started with missionary, and his size and girth were exceedingly satisfying. He was a great kisser and very attentive, sucking my nipples and grabbing my ass to pull me in closer during missionary. We switched positions, with doggy being one of the best sexual experiences of my life. I remember screaming (his size made it hurt ever so slightly, just the right amount) as he pounded me from behind. We also did this thing where he would fuck me from the side, but not from a spooning position – instead propped up on his knees. This shit lasted for HOURS each time, and I had to take breaks in between. He would rest, in me, and we would talk. We had sex quite a few times over the course of the next few days. I would wake up next to that gorgeous body and face – he was a good 12 years older than me but didn’t look a day over 30. Alcohol and wonderful sex for three days, though I never came (never have been able to).

I initially thought that this hookup would help my relationship with my boyfriend back home (great partner, awful sex), but unfortunately we both caught feelings. After I came home we kept this up long distance for a month – I would skype him from the gym in the morning, so that my live-in bf wouldn’t find out. During that month I went back to the region he was deployed in – a significantly more dangerous neighboring country next to the one he was in – and offered to visit (just a few hours flight), but it was a big week for him at work, crazier hours than usual, and he declined. I flew back to the US, and he “broke up” with me a week or so later, after becoming increasingly distant. He told me we had no future because I didn’t understand the role that work played in his life. I was shattered.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

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? I loved it the next day, and still think about the sex. In my stupid mind, I wanted a future with him while knowing that it wouldn’t work out (dicey marriage and divorce history, crazy black ops job that requires long hours in unsafe shitty parts of the world). I miss him and hate him, all at the same time. For a few months I would wake up every morning wanting him, fantasizing about the sex. Still do some mornings.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, Intoxication, To feel better about myself, To feel more desirable, To feel more confident, I was feeling lonely

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? For a long time, no one. I confided in a family member, who told me to end it. The day we broke up, I was headed to a wedding, got wasted, poured my heart out to someone I didn’t know well but subsequently became a very good friend!

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Somewhat

Why do you regret this hookup? Because I let myself catch feelings. I’m usually fine with casual sex, but this fucked me up for a few months. I still have moments of panic and wonder why someone so compatible is impossible for me to be with. I would rather not know that somebody like this exists. It’s excruciating, but I’m not sure I would change a thing. Sort of wish I had been on the pill at the time so that I could have had him bareback.

What was the BEST thing about this hookup? Intense intimacy, his huge cock, his body, gorgeous face, that smile, his technique.

What was the WORST thing about this hookup? Having my heart torn to pieces and trampled on, when all I started out wanting was to fuck a hot black dude

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve reflected a lot on the experience, and realized the need for clear boundaries. If I do this again, I need to evaluate the risks to my emotional well-being more carefully. Still all for fucking hot black dudes, but no more smart ones. No more well-spoken ones. Definitely do not want to catch feelings like this again.

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

All things considered, how NEGATIVE was this experience? Very negative

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? I’m all for it. I’m not sure if I’ll be having any more casual sex moving forward….

What do you think about the Casual Sex Project? Great place to unload this!

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