What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Legal field
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 14
How many hookup stories have you here posted before? One

Trailer Park Trash II

How long ago did this hookup happen? Eight weeks ago

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? I had written about “D” in my first installment. When I first arranged to meet her, I didn’t know her name but later discovered what it was. She’s a 47-yr old Caucasian manager at a trailer park. She’s about 5’6″, 150 lbs, with light brown greeting hair. She’s popped a couple of kids, so she’s what I would classify as average for someone at that stage of life and in that socioeconomic circle. But a nice person to talk with, albeit very simple for someone in my circle.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had met her in her hometown the weekend prior where we went to a hockey game, rented a room, and fucked the night and following morning away. See my other story for the details. I didn’t want to go see her shithole place in the trailer park so I invited her to my place for the weekend. We were going to watch hockey on Saturday, football on Sunday, and fuck non-stop. Does life get better than that?

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? Well, she shows up and says she’s on her period and not comfortable with sex. I’m thinking, “Fuck that. You’re not taking up my weekend without sex”.

I put an afternoon game on and we had lunch and a drink or two. Eventually, we get around to start talking about sex, and she says she’s uncomfortable having sex during her period. That’s never stopped me before, so it isn’t going to stop me this weekend. I suggest we have sex in my big, glass-walked shower, or go up the hoop. I was just throwing suggestions against the wall to see what stuck.

Eventually, I told her we’re having sex, and that she could choose the place (bed, sofa, shower) and the hole. She goes to the washroom, cleans up, and soon we’re in the shower having sex. We then eat, drink, and watch more hockey.

We later in the evening decide to go have more shower sex, and this time she says we’re going to use the other hole. Back in the shower, a little making out, lube up, and up the hoop. Eventually, I go soft and we called it quits. There was nothing earth shattering about the sex, so I’m going light on the details.

We go to sleep and then wake up in the morning. She is an open woman, so I start thinking, if she’s uncomfortable with period sex, how about going over to A.’s place…

So we have to take a step back here for a moment. A. is a bisexual gentleman I met in my town. He lives about 5 minutes from him and he loves sucking cock. I love getting my cock sucked. Bingo! We have a match!!!! I would go over to A.’s place once every 2-3 weeks for a hummer. He knows how to suck cock very slow and sensual, so he makes you last and on a couple of occasions I’ve almost fallen asleep because it’s so relaxing. A. doesn’t like to get semen in his mouth for “safety” reasons, but I love nutting in something, be it a pussy or mouth. So about 2/3’s of the time I just nut away without warning, followed by a “sorry…” as he pulls away after my first shot or two. I’ve always toyed with inviting one of my casual sex partners to come watch A. suck me off, just never proceeded with it.

Well, I wake up and think today’s the day. I had told D about A. the week prior, so when she woke I suggest we go to A.’s place and he can suck me off as she watches and cuddles me. At first, she cautiously agrees, but I can sense she’s a bit uncomfortable with the idea. But eventually, I push her into it during an intermission of a football game.

I text A. and mention I have this friend that wants to come watch but make it clear she’s not up for any play because of her period. He happily agrees and off we go!

I get there, disrobe, and climb on the bed as is the usual routine. D takes off her pants and sidles up to me, and A. dutifully takes his position between my legs. He takes my flaccid cock in his mouth and starts working his talents, and suddenly I’m hard. As he sucks away at his usual measured pace, D is beside me rubbing my arm and shoulders and running her fingers through my chest hair. I had never been in a threesome before, and one FWB that has been in one says one of the most erotic things about a threesome is the sensation of having more hands/mouths on your body than one person can possible have! And she was so right!

After about twenty minutes of this(sometimes I can last an hour with A.!), D leaves close to me and whispers in my ear “This is so hot!” I almost get Ike blowing right there!

Soon afterwards A.’s phone goes off and he gets up to answer it (right in the middle of a blood???). I briefly start chatting with D and my dick starts to go all wet spaghetti with the lack of attention. Suddenly, she goes down on me and vigorously starts giving me head. My tool springs to attention!

A. comes back and we resume the blowjob. I’m not into MM action at all, but a mouth is a mouth, so when A. sucks me off, I always lay back with my eyes closed and pretend one of the trashy Kardashian sisters is plying their only value t society. This time was no different, but suddenly the bed starts shaking and then I feel A. sucking rapidly and aggressively. This has never happened before with A., but I am fearful of opening my eyes to see what is happened out of fear of acknowledging some guy is sucking my dick.

Up to this point, A. had had me on the edge, but I was so fucking hard I could’ve cum. But the sudden change of pace gave me the respite I needed and, without warning, I exploded in Art’s mouth. Except this time it was different – he never pulled away after my first shot – he kept aggressively sucking away also started to gag a bit. But I kept my eyes closed as I came and then during the post-orgasm recovery period. By the time I opened my eyes, A. had gone to the washroom to wash out his mouth. We said our goodbyes and we returned to my place.

On the way o my place, I mentioned to D about the sudden aggressive sucking of A. and how that was different and totally uncharacteristic of his style, and how he kept aggressively sucking me until I was bone dry. Then she tells me “That was me. I was getting tired of watching (it had been going well over 45 minutes at that point) that I grabbed his head and started ramming his face down on your cock!”

I pissed myself laughing! That’s why the bed began to violently shake, the aggressive sucking, the gagging, and the taking the full load came from!

When we got back to my place, it was around 5 pm and the game was over. At this point I get the weekend of play was over so I wanted to boot her out and relax. I fucked her once more, helped her pack up, and bid her a good farewell. I held off on inviting her for the following weekend as well.

But that only lasted a few days….

Catch the third installment.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 was ambivalent about asking her back the next weekend as it was the last weekend before the Christmas break. She was a good person to talk to and we enjoyed watching sports and fucking, but in the end, it was a meaningless relationship because we were very far apart on the socioeconomic spectrum. She very much enjoys my company because I cook exquisite meals and treat her like a gentleman (which I do with all my women), but we both know we’re only together for the sex.

Nonetheless, by the time Thursday rolled around I invited her back for the final weekend before Christmas.

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

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? My friend Jen who we talk often about our sex lives. She’s the real life Casual Sex Project to whom I shared the story!

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? Firstly, it was part of a weekend of sports and sex. I’m 46 and living like I’m half that age! Secondly, it was erotic having D watch a man suck me off. That’s as wild as I have ever gotten, aside from my one FWB that has me fist her with my big farmer hands! Thirdly, this was my first sexual encounter with two people involved (I guess technically it qualifies as a threesome because she did jump in and start sucking on me!)

What was the WORST thing about this hookup? Having to have sex in the shower because of her period. Shower sex can be erotic, but this time it wasn’t because we were in that venue for a reason, not spontaneity.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. After a few hookups, I stopped debating the morality and sensibility of it and focused on what it is – two adults enjoying themselves. Some achieve that by playing cribbage, others by fucking like pagan cavemen!

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

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 moved to this started at age 44 having only a single partner, and her being the only woman. Have ever really kissed romantically. In other words, I was very inexperienced. Since I accidentally fell into the casual sex world, I’ve averaged a new partner every three months on average and have retained a few as good friends (and use their services professionally!) It has clearly built my confidence in encountering new partners, opened my eyes on a part of society that I barely knew existed, and has helped me build a Rolodex in my professional career! How many people have ever been sent a LinkedIn invite from casual sex partners!

What do you think about the Casual Sex Project? Even if no valid research conclusion comes of this, it is providing great entertainment and probably encouraged some to take a walk on the “other” side.

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