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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 and rising
How many hookup stories have you here posted before? 2

East European Big Lady

How long ago did this hookup happen? 2 years 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? The lady was on a local Vivastreet escort website – she had obscured her face with a blurred effect but could see she was a typical larger middle-aged dyed blonde Eastern European type. Several pictures along on her profile showed she was large and curvy and she described herself as a cuddly Romanian. Her rates were low for an hour which is typical for the older mature escort type. I was particularly horny and had a ‘bucket list’ ambition to ride a large lady and her profile gave off a seedy well-used vibe that turned me on. I messaged her for an appointment and discussed some basic services she offered. Her messages were badly written and full of ‘baby’ and ‘honey’ and ‘I give you a porn star type’ etc. We met up later that evening and after a disjointed call to get directions made my way up to a small modern flat.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She met me at the door and looked larger in real life but had a nice smile and sweet eyes. Wrapped in a towel she showed me the bed room and told me to get undressed as she got prepared in the bathroom. She walked back in and after I handed her the cash she offered a massage to get me in the mood. She took off the towel and slipped out of her thong which was twisted up into the tight folds of her pussy. She looked like she had been wearing them for a week but still looked sexy in the poor light of the room. After a really hard massage I flipped her over and exchanged places and gave her a brief massage too and really worked on her back and the rolls of fat. I wasn’t into chubby girls but the weirdness of the experience was getting me hard and I straddled her back.

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? Turning her onto her back, she lay flat staring at the ceiling as I indicated that I could give her oral – she just nodded and lay prone with her arms down by her sides as I lifted her large legs onto my shoulders. The first taste of pussy tasted bad with the urine and ammonia taste indicating that she hadn’t showered before the appointment, but I didn’t want to break the mood and began licking her clean and then worked gently on her clit. She appeared to warm up to this and began humming gently and wriggling her fingers in my hair as I ate her out gently and then faster. I consider myself good at oral and had been complemented by many escort girls even when I tongued them on a first visit with hardly any money changing hands and no chance of repeat business, and I can tell if a woman is faking it, and having hired many escorts could tell the routine when a fake orgasm is being worked on. I wanted to slip two fingers into her to test her wetness and she waived this off saying she didn’t want my fingers in her pussy. She faked her orgasm after 10 minutes and then smiled and said ‘your turn, baby’. Mostly using sign language I got her into a doggy position and with a condom slipped into her.

It was really intimidating fucking with a large ass wobbling in front of me and I usually prefer slim tight girls or ‘spinners’ as I felt my prick was giving more action. She had a well-used style and I was feeling up for dirty sex so got harder as I rode her. Although I felt big and hard my prick seemed to have no traction as it fucked her large pussy despite her beginning to moan louder as I picked up my stroke. After 10 more minutes I flipped her over and pounded her missionary for a bit longer and felt the need to kiss her deeply as I started to really get excited and thrust into her. I’m not a bad looking guy and was surprised as she closed her lips tightly and shook her head to throw off the kisses as I kept fucking her deeply.

After 10 more minutes, I pulled out as I knew her loose pussy wasn’t going to be tight enough to make me come especially with a condom so I pulled it off and laid the condom on her belly unused and started to wank over her big tits that were inked up with tattoos- at this point she started to wake up and looked really pleased at this type of sex as she took the prick in her hand and started to pull my prick onto her tits with more enthusiasm. In broken English she said she loved seeing a man cum and put her hand against my abs and chest saying she loved flat and muscled abs. After a few minutes of pulling me off she started to rub her own pussy and seemed to get really wet for the first time – this really tipped me over and as she rubbed out her orgasm I spumed a large load of cum over her tit breathing hard at the manual stimulation. It was a really good finale to a disappointing session. She smeared the cum over her tits with a big smile as I finished up and I let myself out as she went to take a shower.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

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? She came off the website some weeks later – another middle aged escort probably gone back to her husband or returned to East Europe after making some UK cash.

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, Learning new things, experimenting, Thought it was an important experience to have

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? Paid sex

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 – no need – it was just paid escort sex

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? A little bit

Why do you regret this hookup? Poor effort from the escort as I put a lot of work into pleasuring her – didn’t want and no need for fake orgasm

What was the BEST thing about this hookup? Seeing her wank off

What was the WORST thing about this hookup? Fake oral sex/orgams

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? A little positive

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

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