Room 1412

by Miley

What’s your gender? Woman
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? writer
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 25

Room 1412

How long ago did this hookup happen? last week

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? Dre was a total stranger that I met at a bar. He was super hot, tall, and muscular with a handsome, clean-cut face.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Before I met Dre, the number of people other than my husband I mentally entertained was one—an ex-boyfriend who I knew I wasn’t really into. That fantasy was more about leaving my husband and less about fucking someone else. I had never even come close to acting on it.

So, when an older man got up from his hotel lobby bar stool next to me, I was thankful to eat my salad, drink my one beer, and watch a basketball game in peace. But then, someone else sat down. I think he honestly just wanted some popcorn from the machine by the bar. He was good looking, and I was flattered when we struck up a brief conversation. And only vaguely annoyed when he insisted on buying me my next beer. Then, in that rare talkative mood of mine, and alone and with a drink in my hand, I became genuinely interested in who he was, his whole life story.

So we kept drinking. We talked about our kids, our spouses, our jobs, etc. I thought he was charming and we obviously had some kind of vibe going on. At some point I felt his arm, probably just by putting my hand on his bicep to emphasize some point. I noticed it was solid. All of a sudden, I realized how long it had been since I’d felt anything like that. What else was hard on him?

It’s surprisingly easy to get someone from the bar up to your room if you both understand what’s going to happen. We talked quite innocently about how nice the view was from our respective hotel rooms. “I’ll bet my view is better than yours.” Done.

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? Things got weird that first night. I had twice as much to drink as I normally would, and I couldn’t figure out how to manage my body, my emotions, or my brain. The least invasive thing I could think to do was give him a blowjob. This is a thing I don’t normally love to do. But his dick seemed to me phenomenal. Let’s just say it was big, straight, and smooth. And when motivated, I can give a blowjob that would make you praise god for the entire female race. He sat in a chair facing that nighttime view of a river with a city across from it, which I gather was very memorable for him.
To be perfectly honest, I don’t remember if he came. I know I didn’t swallow. And afterward I remember him over me on my bed, telling me he wanted to stick his fingers in my pussy. I’m not sure if it’s his deep voice, or just him talking dirty, but just thinking about it still sets me off.
But, a strange man looming over me also set off something in another primal part of my brain, the part that says “don’t get raped” and “you have no idea what this man is capable of.” So, I got up and basically pushed him out of the room. Him saying something about what he wanted to do to me, or even just to lie down next to me. “I don’t give a fuck what you want,” I said over and over and over again, with more glee at each incantation. I slept alone, diagonally on a king-sized bed. It was maybe the best part of the whole night.
So, you’d think that would be that. The next day I felt terrible—hungover and traitorous. My husband was home taking care of our toddler all by himself. Plus I had a ton of work to do. I bumped into Dre and it was awkward, I tried to get away as fast as possible. He definitely didn’t seem as handsome. I remember thinking I never wanted to see his stupid face again for the rest of my life. I went back to hide out in my room as soon as work was done. Dre called again (he’d called twice and I hadn’t answered) and this time I picked up. He said he wanted to come talk to me, and I figured I could just tell him this was a no-go, get some closure, and that would be that. I was wearing exercise shorts and my mascara was smeared all over, I was sure he’d recoil in horror of this weepy hag. But he was kind and understanding, he even said he didn’t do this type of thing and was just really kind of unsettled. Oh, and also would definitely be down to do it again if I wanted to, haha. I was firm, even though it was tough to let him go. We agreed we’d keep things strictly professional.
And then I happened to read an article called, “The Emancipation of the MILF” (which had just been published the week before), and readers, it changed everything. Basically, it brought home to me that sexual desire for moms, even those of young children, is NORMAL. It’s also NORMAL to not be getting what you need sexually from your partner/spouse as you both try to balance work and childrearing. And I thought, if I’m going to take on this shame, I’m going to get something for it, not just give a blowjob. Plus I just could not get this guy, his hard body, his big dick, his deep voice, out of my head. I was, to put it bluntly, really fucking horny, and if porn on the hotel TV had been an option maybe I wouldn’t be writing this. Meanwhile, Dre had texted me while he was out to dinner. I texted back asking him to call me. As soon as I heard his voice, I knew I wanted him all over again. I told him I’d be going to bed, but if he felt like seeing me after dinner, he could try to get in touch.
So, then he shows up to my room, I’m in my PJs, little short shorts and a button-up top, which he deemed sexy. As soon as he stepped inside we were making out, hands all over each other. I told him I wasn’t on birth control so we had to be really careful. He told me he’d had a vasectomy. In retrospect, one should not take that as a reason not to use a condom, but oh well. He wanted another blowjob and I told him only if he went down on me afterward. After I came, but he didn’t, we had mind-blowing sex. Me on top, him on top, doggy style, us both sitting up, me on my side with one leg in the air. Toward the end, as I straddled him and he sat on the bed, he stuck his finger in my asshole, which was new to me and created this bright constellation of pleasure around my pelvic area. He told me so many things in that low voice of his, but I mostly remember that he said he liked my hairy pussy, as if it was some conscious choice I made and not the direct result of being a stressed-out working mom too busy to trim her bush. He also commanded me to come for him, which I did, hard, which never happens during sex. He came too. Afterward he told me that next time he wanted to fuck me up the ass, but I demurred, genteel lass that I am. Also, sounds painful. Also, no lube. Also, I DO think my husband should probably get the right of first refusal on stuff like that. Then I told him that this magic only lasts if we don’t spend the night and he left, but with the understanding that we’d do this again the next night.
So, the next day I saw him during work again and it was pleasant. As soon as his coworker left I told him I wanted him to take me to dinner and he told me that all he could think about was fucking me. We went to a work function with a chatty coworker of his. And this is where things get even weirder, as Dre and I are drinking and also trying really hard not to let on how bad we wanted to fuck (which is a really, really hard balance to strike, btw), I get into one of my Deep Meaningful Conversations with his co-worker and the convo eventually turns to sex. I don’t even remember what exactly we talked about, as we were several drinks in, but it was very frank and I think I was trying to school this guy on sex-positive feminism. Amazingly, this did not shrink Dre’s dick all the way up and he took me back to his room this time, and we fucked until 4 a.m. He told me I had an amazing body and seemed surprised to learn I wasn’t five years younger than I was. I told him in my long quest for pornless masturbation fodder the day before I had resorted to looking at benign pictures of The Rock on the internet, as his built body reminded me of Dre’s. We told each other all our unfulfilled fantasies. He called me his dirty little whore and said he controlled me. I told him I was only a whore for him and only letting him think he was controlling me. We were crazy, and fucking like crazy, and marveling at how crazy we were for each other.
I had to do some work, and left his room early, but told him to come say goodbye if he wanted to, which he did. This last time was notable in that we told each other everything we were going to miss about the other person, me: his strong arms, perfect ass, sexy voice, huge dick, charming ways, the view of him over me, shoving his cock all the way inside of me; and him: my chest, my ass, my tight pussy, the milk from my nipples (!), my scent. To emphasize the last one, he grabbed my panties as we were fucking and inhaled deeply, locking eyes with me. That’s hot.

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? Afterward, I felt weirdly tender toward this guy, who was clearly not getting it from his wife, and who worked really hard all day. I remember thinking if I was his woman, I’d give him a massage. But I wasn’t, so I just let my hands run all over his body, and he did the same. We let ourselves have about 10 minutes of that moment to ourselves, briefly discussed if there was any way we could keep this going, realized probably not, and then he left. I did run into him one more time, and we exchanged almost laughably anodyne text message goodbyes, and that was that. He likes Kid Rock, says the word “wiener,” and seemed scandalized that I didn’t have basic cable TV; if I’m honest that’s all pretty lame to me. My husband is definitely the cooler guy.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, To feel more desirable, To feel more confident, It was easy / convenient

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? I told my husband as soon as we had some time together alone. Guess what? He gave not one fuck. We agreed that we could do this sort of thing if we felt like it and if we told the other person first.

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

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 felt good to be desired. The sex itself was kind of magical, not awkward, weird, or bad; it just kept on going, which, for a drunk 45-year-old dude, is pretty impressive.

What was the WORST thing about this hookup? I felt a bit attached a few days afterward, but I just keep thinking: Kid Rock, wiener, he’s probably done this before.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yep. It made me realize/remember that I’m a sexual person, and really good in the sack. I don’t know if I’d do this again with someone else per se, but that option is open now as a “release valve” on my marriage.

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

All things considered, how NEGATIVE was this experience? Not at all 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? Right before this happened, I was very anti-cheating. But I realize now that having this sort of consensual release can actually be helpful in a way, although it is best if discussed beforehand. My husband and I do have wilder sex now, but, to be honest, he’s not the man Dre is.

What do you think about the Casual Sex Project? Thumbs up!

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