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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +/-15 and counting
How many hookup stories have you here posted before? 8

Hot little escort

How long ago did this hookup happen? 2 weeks ago

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

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 found her ad on a common escort posting site. The ad intrigued me as the girl in the pics looked very similar to my wife’s cousin’s new wife whom I find very attractive and have fantasized a time or five about getting with. I could tell by the way that she let me contact her (which I do for the increased anonymity) that she was newer to the business. We set up a meeting. It didn’t go super smoothly but she was flexible and we were able to meet up. Upon seeing her, I could tell that she wasn’t the girl in the pics but she was still very hot. We met at my hotel.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met her in the parking lot as it was a very large place she had never been to before and would never had found her way to my room.

It was a long walk to my room and we got to talk a little bit. She was very sweet and conversive.

Once we got to the room, we began to undress while talking. It had been a little chilly outside so we needed a minute to warm up. She took off her pants and then slipped out of her cute undies. She slipped a condom on me and asked how I wanted her.

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? I told her I would like her on top and she said she would like to leave her sweater on if that was okay. I told her it was fine as long as I could put my hands up inside. I knew the reason she wanted to leave it on was because she was very flat chested and embarrassed. I felt bad for her because, despite her being flat, she was exceptionally hot. It was unfortunate that she was self-conscious as she was amazingly beautiful. Her petite frame only made her look more fun.

I really enjoy having women ride me because it gives me the chance to look and touch. Women, even escorts, deserve to have their bodies admired and hers was certainly worthy to be.

She climbed over me and guided my head into herself. She did the lick and rub right before she put me in but, she didn’t need to. She was already very wet and I could tell she was actually horny.

As she was working me in, I continued to talk with her and asked her if she could cum (I’ve been with enough escorts at this point to realize that most don’t know how to make themselves cum, only how to get guys off quickly). She said she never cums. As this was going on, she had only managed to slide about half way down my cock. I asked her if she could go all the way down but could tell she was struggling. She was very tight and I know I’m a little larger down there so, I try to be very gentle and respectful.

She said she didn’t think she could take me all the way like that and asked if I could get on top. I told her that would be fine with the hope of getting her back on top later.

She laid on her back, placing one of the small round pillows under her head. I looked at her laying there and had to take a moment to enjoy her beauty. I told her that she was gorgeous and she giggled and said thank you.

I got over her and rested back on my knees so that I could watch myself go in. She helped guide me but I really didn’t need it. I got my head started and then got more on top of her properly. She laid there taking me with her head turned. At this point, I thought “here goes another dead fish fuck”. I started slowly going deeper while I kissed her face, neck and nibbled her ears. I ran my hands all over her back, sides and neck. I kept trying to touch her passionately and, to my surprise, she began to liven up and started caressing me. Not the going through the motions caressing but the “I’m enjoying this” type.

I continued to move in her, trying to enjoy myself but also hoping that she might enjoy me as well. I was touching her more firmly now, occasionally running my hands behind her head, pulling it up for her to look as I kissed her face and neck. Her legs began to cinch tighter around me and she pulled me hard towards her with her arms. She was gripping me with her entire body, passionately. It was already the best sex I had ever had with an escort and some of the best missionary I had ever had period.

Just then I felt her. She had exploded in orgasm. I told her that for a girl that couldn’t cum she sure came quick. She giggled and I could tell that she was both surprised and excited. I asked her to look at me and she quickly turned to face me, with what seemed like a surprise to actually be wanting to look at the man that was fucking her.

It had instantly turned into an enjoyable experience. I really liked this girl. I wanted to make her cum again. I asked if she could. She said she didn’t think so. I kind of laughed and told her she didn’t think she could have that one but, at the same time I could tell by the way her body had relaxed that she wasn’t even close to being able to have another.

She told me I needed to cum now. I asked her why I had to cum and she giggled and said “because that’s what’s supposed to happen!” I asked what if I don’t want to. She said because I want you to.

I really wasn’t wanting this to end. Normally escorts are in kind of a hurry to get you done and get gone. I had pushed myself up a little so that I could look at her while I pushed and pulled inside her, enjoying her beauty and her smell (she had gotten very wet and smelled wonderful). Instead of rushing me or looking detached, she kept looking at me and stroking me the way real women do after they’ve cum and their man is still going. It was really sweet. I told her that I wished that she could stay all night.

She told me she would like to but that she had to see a regular that night (some old guy that gave her a lot of money just to spend time with him). She asked if she could come back after that. I told her I had no more money. She said she didn’t care about that, that she would like to come back and spend the night with me.

I asked her if it would be alright if I waited to cum until then. She said “yes!”

I pulled out, gave her a kiss and went with her to the bathroom while she washed herself. The scent was intoxicating.

I left the door unlocked and off the latch for her to return later.

The return was sweet but, by that time we were very tired so, we just cuddled and slept.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

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 hope to see her again. I was in her town on business and haven’t been as of yet. We’re staying in contact, however.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To cheer myself up, I was feeling lonely, Boredom

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? I don’t know / I’m not sure

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? I didn’t tell anyone

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? Getting to teach her a little bit about good sex.

What was the WORST thing about this hookup? Not being able to see her again yet.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

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

Anything else you want to add about this hookup? No.

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 wish I didn’t enjoy this one so much. Normally I don’t give escorts to much thought after the fact but this one has kept my attention.

What do you think about the Casual Sex Project? Good forum.

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