What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? London
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Education
What’s your current relationship status? Single
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)? 18
How many hookup stories have you here posted before? 4

Perfect Escort Lover

How long ago did this hookup happen? 4 years

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? Emma was the name given to the escort on the agency website but she later told me it was Alexia. She looked great as an East European girl on the website which could be trusted not to Photoshop the featured escorts too much and never ‘baited and switched’ their girls – what you saw was what you got! I booked her for a couple of hours and she arrived looking tired and a bit cheap looking with slightly greasy hair and discount clothes including white plastic stiletto shoes. When she got into the apartment and took off her coat from the cold night her body was perfect, toned and gorgeously proportioned. I had a big turn on for Czech porn stars such as Candice Luca and Sylvie Delux who were dark-haired teen-looking slim girls with natural tits and Emma fitted the type perfectly.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I paid her the money and she called her driver to say everything was OK for 2 hours – she said she was nervous about coming into a 5 floor apartment complex as the escort driver waiting outside couldn’t get to her if there was a problem unlike when she went to a house. I tried to reassure her and gave her a glass of wine which she only sipped I guess as she was worried about being slipped a date-rape drug. She said that she’d been eating fast food in the car in a local car park and had spent the previous 4 hours with a guy in a small room who smoked pot all the time with no sex and that was why she looked wrecked. I was pleased she was unhappy about her appearance rather than not care about her looks. After a few more minutes small talk, I got my cock out and slowly started to wank myself into a big erection. She kind of gave a big resigned sigh put her wine down on the table and undressed to reveal her beautiful body that had great skin, toned stomach and no tattoos. I said I wanted to doggie her on the floor carpet which she didn’t like the idea of and insisted on being on the bed. She buried her face in the pillows on the bed and I put on a condom and doggie-styled her for a good 30 minutes until I came. She did very little to push back or join in and was very passive. After I finished I could see she was going to be a waste of time for the rest of the session as she spent ages in the bathroom cleaning up and then keyed her mobile when back in the room – so I let her leave with an hour to spare.

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 could see Emma was on the escort website for several weeks and she had added a video where she looked even better than her pics. I booked her again on a Friday night for two hours determined to make this session better than the last. I could see the spark of a nice personality in her and wanted to see her again. I guess it was also a degree of pride that I wanted her to react more to the sex than last time. When she arrived she seemed happier and more enthusiastic than the first time and gave me a warm smile possibly because she was more relaxed knowing where she was going and who she would meet. She had more of the wine and instead of just fucking her from behind I asked if I could do oral on her as I wanted to relax tonight and preferred the less physical act of licking her out. She was happy with this and it was a relief that she agreed to oral as I hadn’t checked with the agency whether she offered this service. As I put on some soft mood music and dimmed the lights, she undressed and I moved in between her beautiful long legs on the big bed with huge comforters and pillows. She lay back looking down the bed at me with her perfect white skin and legs apart as I slowly kissed the inside of her thighs and gently stoked her tits and fingers as I worked up to her pussy folds and clit. I was really teasing and slow as it was all I was going to do for the session. I was determined to take my time and I think she was surprised she was getting a gentler sex action than the first time I impersonally pounded her from behind. She flinched a few times as I worked out how much pressure from my tongue she could stand on her clit and eventually with soft licks like a cat drinking milk I licked completely from the bottom to top of her pussy causing her thigh muscles involuntarily twitch and her breathing to hitch and gasp as after 40 minutes her orgasm finally hit her. She arched her back and gripped my head between her thighs and I kept up the same tongue speed as I continued to lick her clit hood and drink in her orgasm juices until she climbed down.

When giving oral to some escorts, I found some have delayed cumming or faked a late orgasm just to avoid being fucked by my prick later in the session in order to avoid being penetrated for long. Emma was just a slow girl to orgasm. She relaxed into the bed but didn’t say anything and then looked down at her pussy and the wet patch on the bed spread – “It’s a lake”, she laughed as she saw the dark stain from her pussy juices.

I booked Emma more or less regularly once a fortnight for a year and although not a guy who likes submissive sex I spent most of the time giving her oral searching for her perfect orgasm. After one session she said it was the best orgasm she ever had and where did I learn to do that. She didn’t need to say it and it really boosted my ego. She was increasingly relaxed and friendly. After a gap of a couple on months where I went abroad she asked me when we met up whether I “missed her” pointing at her pussy – I laughed and asked her if she missed my tongue. She had better and longer orgasms just from being licked (no fingers in her pussy) as the months past and said it was the only way she could cum as penetrative sex didn’t get her off. I was happy fucking other hook ups and escorts to get myself off and just worked on Emma’s perfect oral orgasm when I saw her. After one session she became all ‘girly’ and romantic putting her hand in mine and saying how small her fingers looked. She sang gently to herself in the bathroom as she showered clearly enjoying the afterglow from her orgasm. Eventually, she asked if we could be friends and I agreed to see her outside of the agency and off the clock. I kept paying her but she would stay 4-5 hours watching TV and talking between oral sessions. She began to suck me off and fuck me conventionally now during these sessions but still orgasmed exclusively from extended oral.

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? Emma disappeared off the escort website and she had talked about leaving escorting. She knew I didn’t want a relationship and was too old for her. I had her mobile number but didn’t call it as I believed if she wanted to hook up again, she could make the move. I heard from one of the other agency escort girls about 18 months later that she had had a kid with one of the male escort agency employees and was working as a barista in a coffee chain. I wished her well and was pleased to have worked on her perfect orgasms.

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

What were your motives for this hookup? Attraction to partner(s), To feel better about myself

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? 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? 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? 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? Changing Emma’s attitude and really working on exclusively pleasuring a woman for a change

What was the WORST thing about this hookup? The start of the relationship – bad start

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

All things considered, how NEGATIVE was this experience? A little 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? It works on many levels

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