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What’s your gender? Man
How old are you? 50’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Medical
What’s your current relationship status? In a serious relationship (open)
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)? 50+
How many hookup stories have you here posted before? A few

Bareback Escort

How long ago did this hookup happen? 6 months ago

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

How would you best classify this hookup? Paid 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 was traveling alone for a few days and felt I needed some company. The wife and I haven’t had sex much due to her health issues and she has told me to make sure I was satisfied. I called her after work to say goodnight and talk about my day. I wanted to know how she was feeling. She asked if I needed anything while I was away. We’re pretty honest with each other so I told her I really wanted some female companionship but I’d be ok.

She suggested I go online and find a paid escort since she knew I’d never develop any feelings for her and that would take care of my needs with no emotional attachment. Her only request was that I tell her the details.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went online after that and did a few searches on some sites. I looked for an “older escort” who had good reviews and appeared reputable. I found one who looked promising and gave her a call. I suggested she meet me at my hotel, which would be safer for me not knowing her to which she readily agreed.

She asked if I had any “dress requirements”. Now being the visual person I am, I asked for a miniskirt, or very short skirt, thigh highs, heels and no panties preferred. Her response was “no problem”. She asked if I liked a lot of makeup or a little and I said, “the more the merrier”. To which she replied, “We’re going to have a great time, I know exactly what you want”.

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? She showed up at the agreed time looking exactly like I had hoped. We sat at the bar and had a few cocktails to get to know each other. She was actually quite charming. Medium build, blonde hair, 36DD breasts and appeared to be in her late 40’s. The typical cougar type woman I like.

We were getting pretty handsy at the bar when she suggested we go to my room. I got us each another cocktail for the road and we went up to my room. She excused herself to the restroom to freshen up where she found the envelope with her name on it. I had left considerably more money in there hoping for a better experience. I guess my tactic worked based on what followed.

She came out smelling just wonderful and sat on the couch next to me. “Tonight is all about you so don’t even worry about me” at which point she undid my slacks and got on her knees giving me a stellar blowjob. I told her I didn’t want to cum that quickly to which she replied, “We can go again and if you have a problem going a second round I have plenty of tricks to make sure you can. I asked her where I should cum as I felt I was close. All she said was “In my mouth” which I did and she swallowed every drop. She took a drink of her cocktail and we just cuddled for a while.

She wanted round two and I wasn’t quite ready. She said not to worry and went into her purse to get some lube and a cock ring. She was able to use the lube to begin to get me hard and then slipped the ring on me. The longer she did it the harder I got.

She then straddles me facing me, at which time I felt she had no panties on and a sopping wet shaved pussy. We were kissing intensely as she ground her pussy onto my cock. I was enjoying the hell out of this and she knew it as she teased my swollen cock with her pussy lips. Her wetness combined with the lube made for an intense sensation.

“We can do it if you want” she said to which all I could do was nod OK. At that moment she positioned herself so I slid into her pussy easily. I was amazed how hot it was and enjoyed the moment. She rode me for a few minutes when she tensed up and said she was cumming. At that moment she jumped off and squirted what seemed like a gallon on me. This easily was the hottest thing I ever experienced.

She put me inside her again and with the combination of the lube and cock ring it took me forever to get ready to cum again as I felt it building. “Where should I cum?” I asked her. Her reply was simply, “In me”. With that I let lose whatever was left in me. She cuddled with me for a bit until I went soft, then jumped off to head to the bathroom to clean up and returned with a moist warm towel me. She offered to stay the night but having to leave early wouldn’t be fair to her. She told me if I’m ever in the area again she’d love to see me.

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? I told her that I’d love to see her again if I was in the area to which she enthusiastically said she would too

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

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? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My wife. I told her everything and she was happy I enjoyed myself.

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having sex with a pretty older woman

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Love the site and peoples stories

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