Author: Torontosophisticate

[MF] Tamil FWB – The Deepthroat

This is another installment of my experience with a Tamil girl as an FWB. To recap, sheltered due to culture. Was into white guys, had to meet with me in secret. Had done stuff before, but really vanilla, and it was basic vanilla. So today we will be going over her first deepthroat/blowjob to completion.

For context, we would be talking over the phone. We didn’t really chat on AFF anymore because we wanted to be exclusive to each other (we were both in our feelings and we knew it would never work out but we pretended like there was something and managed to convince ourselves). Anyway, this was a week after our first get together. And we were going over experiences, what we’ve done, what we haven’t (for her it was pretty much everything) and what we want to do. Fast forward, our next meet up she agreed to go down on me for as long as I went down on her. Little did she know that I could go down for a loooooongg time. So that was nothing for me and really what I wanted to do is get her in a position where she could suck me to completion and get her to practice on me and get better with her skills so I would appreciate it more in the future. Yeah, more of that delusion I was referencing earlier. Read more »

[MF] My Tamil FWB

This is a brief account of my time at 26 y/o with my Tamil fwb. It lasted for a year, and it was fantastic.

I met her on adultfriendfinder. She was on there because she was Tamil, traditional home life and all that (if you are Brown then you know!) but this was also a Tamil woman in Toronto in the mid 2000s. So if you know that time and why it was significant for Tamil people….Anyway.

She was curious. Curious about being with a white guy but had to keep it secret as she didn’t want her family to know.

So we are chatting on the messenger and finally I get her email. We have been chatting for a couple days. Nervous about meeting. Knowing the air of sex was in play. She was with only 1 other guy, a brown guy and she said he wasn’t that big and he came too fast and that was it (a shame for her first time). So I tried my best to reassure her and also turn her on through message to the point where she agreed to meet me. Read more »

[MF] Daycare adventures #6 – a coworker

Alright alright, I know it’s not a mom. But she was older then me, not a MILF (no kids). But fuck it, who cares. It happened and I’m telling y’all about it. :)

Also, I keep saying this will be short and end up writing a mini novel. So in that spirit, I’ll try and keep this short and fail miserably at it.

For context, this happened midway through my daycare career. It was a community centre that had multiple services running out of it. This is a coworker from one of those services (So not a daycare worker herself). We had huge sexual chemistry but didn’t do anything due to work. So this happened as she was leaving to take a job elsewhere.

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Fast forwarding this to our 4th date. We had talked on the phone (no texting remember, 2000s), we were very sexual with each other. On all our previous dates. We had made out in her car. Felt each other through our clothes. She loved to tease, loved it. I was a walking hard on…always was but even more so now that she would edge me. And for context, she said that she was super tight. Read more »

[MF] The time I had sex with a woman with only 1 leg.

Ok, lets have some context. I found out later (the day of, in person) that she had a prosthetic leg. I’m not going to glorify this (anymore then I am), nor do I have a fetish for this. It was just a unique experience I had when I was younger and now I’m sharing. I’m 19 at this time. She was 19 as well.

So this was a time long ago, when the dinosaurs roamed the Earth. I was chatting with this girl online on one of those chatting websites. Could be ratemybody, facethejury, Hot or not, etc. Anyway, we are chatting through messenger and getting all flirty, sexual and we agree to meet. She plans on coming over to my place. All the arrangements were done online. Texting wasn’t really a thing back then. We still had those phones were “send nudes” required the “S” button pressed 4 times in a row.

Fast forward. She gets to my place and she looks just as she advertised herself as. 5″2, almost but not quite a BBW, Fillipino, really big-full breasts – at least 38 DD, slightly tan skin, long black hair, hazel eyes. Dressed casually in a long tshirt, faded jeans and sandals. She had a very slight limp which I didn’t comment on, just noticed at the time. Read more »

[MF] The night I had with a MILF from an old 2000s website

So if you’re old like me. You remember those websites that allowed you to see faces/bodies of people and you can rate them from 1-10 and you’d get an average rating and people would post provocative pictures to increase their score, etc etc.

Well this is one of those sites. I won’t say the real one, but if you remember the website FaceTheJury it was pretty much identical to that. Anyway, they had forums to talk to other members and quite often they got sexual. Anyway, I was 25 and talking with this woman from Barrie (Yeah I know, Barrie!) but she was cute and a nice body on her. Long story short, she decides to come down to Toronto and meet me.

Friday night comes. She lets me know she is around, I greet her in her car. I already knew what she looked like. She was 39 years old. Reddish brown hair. Green eyes. Cute round face. Pouty lips. About 34 C breasts and good height/weight proportion and curvature. She is also wearing a very sexy hat, I told her that it was a thing for me…women wearing hats, still is. Read more »

[MF] Daycare mom #5 – The Nigerian mom

For context, this mom took years to arrange. Lots of flirting, talking, getting to know, comfort levels, etc. She knew about the other moms and that’s the only reason how this got brought up for me to have that level of conversation with her. On to the story.

This mom was born in Nigeria (pretty sure, or maybe Cameroon, no wait…Nigeria, yes!). Anyway, she lived there as a child, came to Canada as a teen. Spent enough time here to get “Westernized” I suppose is the term when you start wearing different clothing, enjoying music and trends from North America. And basically start living the non traditional lifestyles (to a point) from the country you were born from your their parents came from.

I’ve heard from a lot of children of immigrants to a country (male and female) the struggle to listen to their parents and follow the old/traditional ways and live in a society thats completely different and to follow the trends and lifestyles of their contemporaries growing up. Also, the acknowledgement that their life right now is different then the life their parents lived and how the parents try to get their kids to live the life they led – if that makes sense? And the friction that causes when you don’t want that life. E.g. date outside culture/religion, the pressure to be a doctor/nurse/lawyer/accountant etc. Read more »

[MF] Daycare mom #4 – the Indian Mom

So my stories are getting long. I will endeavor to shorten them for brevity.

For context, know the first couple confessions I made. So to shorten this up. We got talking because she heard about the first few moms and mom #2 told her I’d be down.

So this Indian woman. She was half Malayala (spelt right?) and half Tamil. She came here to Canada when she was 10 I think. She is “Westernized” as the phrasing goes so she wasn’t the traditional Sikh or Tamil or Punjabi woman you would see in a Bollywood film. She would come to the daycare dressed amazing but in western style clothes. One thing I could say about her. She was always dressed very well. Made her very attractive the way she took care of herself and her sense of fashion. She was 5’6, average weight/proportion, about 38C breasts (her 2nd standout feature), flat bum, very pretty face and some of the biggest most beautiful brown eyes I’ve ever seen (yes it sounds like I caught feelings, I was crushing at the time), and long black hair that hung down to her lower back and her skin was a nice brown skin colour. Read more »

[MF] Daycare single mom #2 – The Caucasian

Sounds like a sequel to a bad, low budget horror flick.

I have received numerous requests for other ethnicities and I will post them. I promise. I’m posting this one here, now because it sets up my others which will become relevant later on.

On to the encounter.

So this woman, she was I suppose the Alpha-Queen mom of most of the daycare moms that we had at the time. Due to her being social, blunt, charismatic, open, nice, etc etc. Other moms gravitated to her and she was the planner and all that jazz and they all listened to her and got involved in her ‘things’.

She was a waitress (That’s important if I post other experiences I had with her), about 5’4 in height. Slim. Blue yes, long brown hair that went down to her waist. I would say a 36 B cup. Attractive. Her crowning achievement was her ass. I will never forget it. Must be from all the walking and standing around at her job. This ass was sculpted in heaven by all the Gods and gifted to us mere mortals for viewing pleasure. The perfect apple shape that stuck out from her slim body. She had 2 girls in the childcare at different ages so she was someone I knew for a year or two and we got along great. I was always wanting to chat her up, flirt a bit. Just to sneak peaks at that ass. Read more »

[MF] Daycare single mom #1 – The spanish one

Thanks for reading and responding to my first post about this. Felt good to share and hopefully you enjoyed reading it.

This is the not so long true account of the first mom (I think – memory is a bit hazy on the order) I hooked up with from the daycare I worked out.

She was Spanish – From Spain originally and immigrated here to Canada as a teen so she had a combo of Canadian (western traits and Spanish). I would say she was a mix of conservative and freaky. It helped that her 2 children loved me. So it meant interacting with her and having conversations with her very easy at the end of the day. Hell, the youngest would ask mom to invite me over to dinner. It was cute.

Anyway, she was about 5’10, slightly tanned skin tone. Black hair, brown eyes. Very perky breasts for her size (or maybe I”m just not knowledgeable on that). They were I believe 32D or 34 and in her 30s. A little extra padding around the middle but nothing to be ashamed of and actually gave her some great curves. Liked her jewelry but didn’t flex on people with it. And as time went on, I noticed that her tops got a bit tighter and things got pushed up a bit higher. Or was it the horndog in me? Read more »

[MF] As an (M) daycare worker, I had sex with multiple single moms

So this happened for 6 years. About 2001-2007 approx. When I was about 20-26 years old. I was in the best shape of my life at the time and pretty virile. I’m 6’0, white, 10% body fat (or so it seemed) and athletic with short spiked hair (hey, don’t judge, it was the early 2000s for this). And to top it off, I was working with school age children in a daycare setting.

Add to the mix, a geographic area that had a lot of single mothers who had fathers(fathers of the children they gave birth to, for clarification) leave them either before or after their children were born. So in my opinion. A lot of sexually pent up women who couldn’t necessarily get out of the house/apartment on dates or hookups or whatever.

For me it was life changing. I got to experiment with certain things. I had about 8-9 women in that span specifically of moms from the daycare. It was a big daycare with an extra afterschool component and summer camp added in, so lots more moms then a typical daycare setting. They were my first non white women. I had sexual relations with black, Indian, Spanish and mid-east Muslim. Read more »