Chicago Chicano Shenanigans

by Boston Traveler

What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Management
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Voracious
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 5

Chicago Chicano Shenanigans

How long ago did this hookup happen? This week

What was your relationship status at the time? Single

How would you best classify this hookup? Group Sex

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? I slid into the bar at the CHI Athletic Club and strategically chose a stool next to a striking Latino woman. At first glance, I would have guessed she was in her mid 30’s, but up close the hands and eyes revealed she was closer to 45 or so. She was a pretty woman – average height, dark full wavy hair, chesty without being silly, great legs coming out of a short stylish pleated skirt, stylish heels, and, just above them, an anklet with a male, male, female charm. Game on.

I ordered a drink and saw a conversation opener. We got to chatting and I discovered she and husband were in town for a niece’s college graduation. Her husband was “upstairs napping” as they had a long day. I know bait when I see it, so I bit, and after another drink, asked her plans for the evening (it was around 9:30 pm). She equivocated and I suggested wine and a movie in my suite so as “not to disturb her husband”.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I ordered a bottle to my room along with some noshes, settled the check, and we were gone. In the room, she became a bit more nervous. I began to suspect she was a bit new to swinging and played pretty chill. After about 45 minutes of wine and GoT (hey, season 8!) I told her I was going to shed my work suit. I went to the bathroom and came out in a nice fluffy robe (the primary benefit of a nice hotel) and tossed the other one to her. She looked at me and said I looked comfy, smiled demurely and took the robe to the bathroom. I heard the shower run and she emerged a few minutes later with her hair tied up and back, a bit of water on her neck and legs, clothed in the robe.

At that moment she got a text and upon reading it, said her husband was up. She looked at me in an attempted coquettish manner and wondered what she should tell him. I have been down the amateur cuckold road before and decided this hot MILF and her clown husband needed professional instruction.

I walked over to her, undid the sash to allow her body full exposure to my gaze, lightly stroked a nipple, and kissed her. Then I told her to tell him to “come to my suite and watch you star in a love story”.

I’m not sure what she texted, but it was fast.

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 embraced and I explored her body. She kept shifting from bold and confident to shy and retreating, and I was now fully convinced they were novices at the game. I splayed her out on the bed, legs akimbo, with two of my fingers searching for the g-spot when her hubby knocked. I let him in and didn’t even say hi before I went right back to fingering his wife. I took my robe off and handed it to hubby, telling him to get comfortable as I sank my cock into her.

He got naked and I saw the problem. He was of average length but thin and with a tire hanging over his cock. I am reasonably fit, average length, but thick. I filled her and went to town – legs over my shoulders, pounding her pussy, thumb working her clit. She was humming and cumming and I noticed hubby stroking his skinny cock with two fingers while he watched.

I was getting the impression that humiliation was part of it so I withdrew and pulled her to a sitting position and shoved my cock in front of her face. I told “George” to get his cock over here and had it next to mine and in her face. I said something to the effect of “suck the man, swat the sissy” (really – not pre-planned) and she took me all the way down while slapping her husband’s dick. It was pretty humiliating, but then he came!

I put the flabby sissy boy through a bunch of sick stuff. I had him clean up my cum from his wife’s cunt. I had him lube up his wife’s ass with his tongue so I could fuck it. I Then had him eat his wife’s pussy (her on top in a 69) while I fucked her ass and she sucked his cock. He was an enthusiastic participant in his humiliation, I was an enthusiastic defiler of this MILF, and she was simply sex deprived.

How sexually satisfying was this hookup? Somewhat

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? I got tired and sent “George” back to his room but kept his wife. I remember just as he was about to leave I looked over at him and sank my cock into his wife’s ass (she was on the edge of the bed on all fours) I asked him point blank if this was their first time and pointed at the anklet. He admitted that they bought the anklet last weekend and that this was the first time they had done something like this.

I stroked in and out of his wife’s ass a few times and said: “Marizette, is this the first real cock for you?” She looked back and said “no”. I looked “George” in the eyes and said, “you seem to enjoy it so get used to real men using your wife.” I smiled, said “I’ll have her back in the morning”, and proceeded to hammer her

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Power / Dominance, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

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

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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? No one

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? I don’t know / I’m not sure

Do you regret this hookup? Very much

Why do you regret this hookup? “George” was along for the ride. Late 40’s, fat, probably a professional failure, no confidence. I could mock his cock but truthfully he was probably pretty average. I am thick but hardly a porn star.

The poor man just lacked confidence. I’m not sure if I fulfilled a fetish or walked into a situation his wife was looking for. I am confident she had fun, but I am a bit worried it was the end of the road for George.

What was the BEST thing about this hookup? The sex! And being an Alpha. In my day to day life, I am an alpha but my profession demands that I hide that. This was raw – “clean my cum out of your wife’s ass”. I enjoyed the power trip.

What was the WORST thing about this hookup? I think I broke “George”.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? No

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