Catalina's Week of Pleasing Pillow Princesses

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29-year-old Catalina is a friendly and soft-spoken African American New Yorker who shared an apartment in Harlem with a childhood friend. She spent most of her days working in a retail clothing store and lived a single life by choice, using some of the perks that came with it to justify her secretly raunchy and somewhat random sexual encounters.

Being in the size 12-14 range, Catalina matched her curvy shapes and 6ft height with smart casual clothes that looked great on her. She proudly proclaimed herself a small BBW with a family heritage from Ghana. Her close friends and family lived scattered around New York and were unaware of her secret sexual side for over 4 years.

Through several websites over the last couple of years Catalina lived in a world of casual encounters and more specifically, meeting with the metaphorically coined ‘pillow princesses’ and ‘queens’.

At some stage back in her first year in retail, she worked at a particularly quiet store during the weekdays. It left her with a lot of free time in between customers to study or do other things online.

She discovered what casual encounters were and was hooked ever since. Especially the women 2 women sections, which were full of descriptive ads from both young and old women, some fit and some on the extra, extra BBW side. All from various Manhattan, the Bronx and Brooklyn suburbs and asking to meet other girls discreetly for what they kept referring to as ‘fun’ or ‘discreet play’. Some suggested getting a hotel room, others could ‘host’, and some were wild enough to meet in public. It’s captivated Catalina who let her mind run wild with raunchy possibilities, she never cared much for a label and felt an attraction to a lot of people if the context or feeling was mutual. And when one big website got taken down years ago Catalina quickly found its successor and was ‘still looking’ as they say.

Using an anonymous email account, Catalina met different kinds of women and over time also made several ongoing ‘NSA’ friends – No Strings Attached. They were girls who had boyfriends but made up a fake background story for Catalina and pretended to hang out as just friends.

Catalina was not sure why she enjoyed meeting so many random women for sex, but the monotony of her first retail jobs and the mutual interest for discreet lesbian sex from the ads contributed heavily in the beginning. For weeks on end she first just read everything and fantasized, building up her confidence and curiosity to find out more about these so-called princesses. Until one day she stopped caring anymore and got involved. What little experience she had from drunkenly fooling around with girls back when studying she made up for with a healthy dose of reading lesbian erotica and a curious attitude to life in general.

The first woman she messaged with turned out to be a flake, a term she got used to over the years as many girls were ‘teases’ and found it challenging to follow through on their lesbian fantasies. Catalina sympathized with them and did not take it personally if they stopped replying. And even worse, some women were men in disguise. Once Catalina found out she stopped talking to them.

But that first woman sparked a courage in Catalina, and she replied again, and again, and again until she was comfortable to meet her first – a married woman in the corner of a quiet car park. It was a bit clumsy, anxious and bordering on sleazy, with both of them inexperienced and unable to relax. She faked her orgasm to make the woman feel better and was not even sure if she was doing that great of a job returning the favor. It was an average first meeting, but Catalina realized quickly that with some practice and skill she could enjoy it with the right women.

That first encounter lead to many more. The following day-by-day was one busy week in the early summer months for Catalina, balancing her secret lesbian encounters with the rest of her life.

MONDAY

The ‘Stepdaughter’

Catalina’s planning for the week started from the Sunday evening. Her manager emailed through the roster for the week and they asked her to work Monday to Thursday from 11 AM to 8 PM and close the store. On Friday she would have a 9 AM to 430 PM shift, and Saturday just a short 9 AM to 1 PM.

The Monday before was uneventful both during as well as after work. And Catalina thought that week would be similar. When she woke up, snoozed and was about to start getting ready for work her gut feeling told her to check the discreet email for any responses.

An email from Irina, one of Catalina’s favorites, read –

'Hey x I’m back in town and free tonight if you can come?'

Catalina giggled and checked the time it came in. It was that same morning but early, around 6.25 AM. She replied.

'Hey! Glad you got in touch, yes I am free. Same time and place? X'

Irina was an older Eastern European woman Catalina already met with 6 times by replying to her ad. She never told Catalina where she was exactly from except that she normally lived and worked in Boston. The trips to New York were for work and they luckily paid for a nice hotel. Irina was also into the online encounters and explored during those work trips away from her husband and normal family life. Catalina got along well with her the first time and they agreed to keep meeting when Irina came to New York.

Irina liked to role play as stepmother and stepdaughter when in public since she looked quite mature. She was in the mid to late 40s and explained to Catalina the first time they met that she hated the attention from other people whenever she was with a younger girl. Irina did not like random hook ups and liked to get to know her “stepdaughters” before bringing them back to the hotel. That usually involved going out somewhere and being seen in public, as well as staying the night with Irina and enjoying the hotel’s complimentary breakfast. During these public moments Irina never wanted t

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Written by Read Me Tonight
Uploaded September 26, 2020
Notes 29-year-old Catalina from Harlem NY worked a full-time job in retail and managed an active sex life by discreetly meeting women online. Read about her day-by-day retelling of one busy week where she pretended to be a business woman’s Stepdaughter, met a lesbian student for Netflix & Eat, participated in a threesome with a Filipina while her boyfriend watched and more.
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