Toronto Escorts

Quickest sex with civy

tier3

Dabbler
Aug 11, 2022
30
46
18
How did it happen and was it enjoyable?
When I was in college, I had a girl I never really knew that was into me. She was dropping hints here and there over text, but then one day she straight up texted me "I don't care where or when but let me ride you"

The next morning I pulled up to her house, fucked her in her moms bed for over an hour... and then when to class.

My easiest and quickest to date... with 0 effort. Might I add this was the most time I had ever spent with her.

Was it enjoyable? Absolutely yes. She was so wet you could see it on her panties before she took them off.. plus she had a BOOTY.

Oh and her moms bed had a bible on it. Can never forget that.
 

IM469

Well-known member
Jul 5, 2012
10,894
2,170
113
Visiting our office in TO. It was a small office of ~ 12 people. Everyone was out but the young blonde receptionist and I wish I could remember the conversation but she ended up giving me a blow job in the office. We hooked up later when she attended a course in NYC. She was engaged and wanted to have a little fun before she tied the knot. No idea what happened to her. We parted and went our separate ways.
 

Scholar

Well-known member
Mar 14, 2006
565
672
93
Visiting our office in TO. It was a small office of ~ 12 people. Everyone was out but the young blonde receptionist and I wish I could remember the conversation but she ended up giving me a blow job in the office. We hooked up later when she attended a course in NYC. She was engaged and wanted to have a little fun before she tied the knot. No idea what happened to her. We parted and went our separate ways.
Years ago a buddy came to visit with his g/f and one of her friends. Friend wanted to go to the store and asked me to walk her out as I had a few large dogs at the time. Get to the bottom of the stairs and she says she wants me to fuck her so I bent her over the couch. When she got back from the store we acted like nothing had happened. I wish I'd pursued her a little more as she was really cute but at the time I was thinking, "If she just did that with me, how many other guys get the same treatment?" and I didn't bother.
 

GameBoy27

Well-known member
Nov 23, 2004
12,602
2,481
113
Ended up having sex with quite a few civvies in the 2-4 hours after meeting them. My wife included. Always loved those encounters, so hot.
 

HobbyHorse

Active member
Nov 14, 2009
788
65
28
Blind date met me at Union Station after work.
Very beautiful.
I just looked at her and a strange certainty passed over me about what was going to happen…
We walked across the street to a restaurant in the Royal York, ordered martinis, each pretending to read the menu.
Returning from the washroom I just grabbed her hair, gently tilted back her face and kissed her.
I dropped some bills on the table and we left without eating, grabbing a cab to her mid-town home.
In the cab her shirt was open and her bra came off. I ended up tipping the driver bigly to compensate him for our lack of discretion.
It turned out she had nothing to drink at her place, but it did not matter.
It was a terrific summer night. We fucked quietly on some lawn furniture on her back deck.
Then we went to her bed and did it again, but less quietly.
It was a Penthouse Letter come to life (that being the era.)
 

dchoye

Member
Jun 7, 2007
75
70
18
My most memorable one was when I was young and inexperienced Not seen any SP and only been with 2 girls before I met and exchange phone numbers with very attractive woman who was in her 30s at the gym. I was in my 20s. Went on a date next day and at the end of the date she gave me a really good long BJ. I was a good boy back then and didn’t believe in sex on first dates so it was taboo yet exciting for me . She was obviously very experienced and ready to have sex
 
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stephenp

...
Feb 28, 2006
1,105
4,177
113
My most memorable one was when I was young and inexperienced Not seen any SP and only been with 2 girls before I met and exchange phone numbers with very attractive woman who was in her 30s at the gym. I was in my 20s. Went on a date next day and at the end of the date she gave me a really good long BJ. I was a good boy back then and didn’t believe in sex on first dates so it was taboo yet exciting for me . She was obviously very experienced and ready to have sex
Did she stop at the bj?
 
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drstrangelove

Well-known member
Mar 26, 2004
1,170
252
83
Went to a disco with a friend where we met his girlfriend and her friend. I commented on her 38's, she confirmed and suggested we go to my place. We did, had sex then I drove her home, never to see her again.
 
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Kurt

Active member
Jun 20, 2002
753
240
43
54
Somewhere between here and there
Years ago - late 80's a girl in class ask for a ride home - it was an evening class so late and very cold that night - it was not on my way home and she offer me I hesitated but she offered a BJ - I thought she was joking. She was a cute short stacked girl. So i drove her home and before I got to her house she told me to park in the school parking lot and game me a great BJ and swallowed. This went on the rest of the semester - it never went further then her blowing me and playing with her tits and fingering her a couple of time - she had a boyfriend and wouldn't do me. Never saw her again after that semester.

Another time at a conference on the way back to my room was walking with a cute MILF and turns out her room was across from mine and about an hour later she knock on my door - I open it and before I knew it her tongue was in my mouth. was an interesting night. she snuck out at some point and we never repeated.
 
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Ceiling Cat

Well-known member
Feb 25, 2009
28,269
1,152
113
I arrived at a lady friend with benefits place, the plan was to go out to dinner and then come back to do some humperoni. She buzzed me in the building, when her door of her condo unit opened I could see the items that were in a closet were all moved out. What had happened was the person in the condo upstairs had over flowed the bathtub and flooded his floor. The water has made its way into his closet and soaked the closet floor then made its way to the lower floor. She was called mid afternoon at her work to deal with the situation but did not call to tell me. The female concierge came to tell her the workers were upstairs cutting out all the wet drywall, after they finished they were coming down to do the same at her condo unit. My lady friend asked the concierge if she would be with the workers and how long would it be before they would come to her condo unit. She said yes, she would be with them and workers would be there in 10 -15 minutes. The female concierge went back upstairs and when the door closed we both ran to her bedroom, she kick off her high heels and I unzipped.
she started up my motor and she got on her knees on the edge of the bed. She unbuttoned her blouse and I pulled her leggings down. I flipped her tits out of her bra and humped her from behind. We accomplished the task without taking any clothes off in about 10 minutes. As we finished there was a knock at the door.
 
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IM469

Well-known member
Jul 5, 2012
10,894
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.......... I wish I'd pursued her a little more as she was really cute but at the time I was thinking, "If she just did that with me, how many other guys get the same treatment?" and I didn't bother.
Really cute ...? I wish I had that will over my cock. I may not have formed a long term commitment but she would definitely have made the rolodex.
 

massman

Well-known member
Sep 8, 2001
4,291
2,550
113
My GF when I was 17. I was very inexperienced, she less so I think. We had made out and fooled around with clothes on a number of times. Went away for the weekend to a friends cottage, and ended up in our own bedroom. Made out, clothes came off, I think I lasted 4 pumps. We did it again a couple hours later, I lasted 5. Is that what you meant by “quickest”?

After that trip she stopped answering my phone calls. I couldn’t figure out why? 🤷‍♂️

(😢😢😢)
 

Cbr20152012

Well-known member
Aug 7, 2023
425
830
93
I enjoy sleeping with strangers. Often find myself with someone despite having only met them an hour prior. Not sure I do it weekly, but several times a month.

Always the same. Meet a stranger at a cocktail or a lobby bar. Smile. Say hi. See if our conversation is engaging. Be cognizant of strong eye contact. Watch for changing body language. If she is leaning in, has unbuttoned a button or we have good body contact I explain that I love meeting people this way, I explain why I like it and the emotion and experience I get from it. They are either excited by it or not. If they aren’t I pivot so that it isn’t uncomfortable, finish my drink and wish them good night. If they are, we hook up. It works well. Just need to dress nice, smile, be positive, be interesting, and be honest/genuine.

absolute fastest, long time ago. Slightly older woman smiled at me at a club. I smiled back and said, “your place or mine”. She said, “mine”. Done. Never even asked each other our names. Hot.
 

Mandalorian

My friends call me Mando
Nov 13, 2020
772
1,309
93
This past Feb in a Chicago convention. Sat in the lounge reserved for special guests and volunteers with open bar and buffet. I was alone on a leather easy chair taking a load off my feet with a whisky after a long day. Slightly older lady was sitting across from me in a very nice skirt and suit jacket. People all around us, I caught her eye, we smiled. After 30 seconds I walked across and sat next to her and asked how her day went. 2-5 mins of commiseration and I put my hand on her knee and leaned in and we kissed. Never tried this before and I was shocked at my boldness. Suddenly she breaks away and said her co workers nearby might tattle on her so we went and found an empty meeting room and slid my hands up her skirt to a sopping wet pussy and proceeded to eat her out. It was so hot! Made plans later that night for drinks at her hotel lobby and spent the night.Best convention ever!
 

Caveman

Well-known member
Sep 9, 2001
1,199
333
83
Met her on a late flight from Atlanta to Memphis. She was already a little tipsy from her previous flight and started telling me about her life story. Turned out she was coming home from her European vacation with her best friend who lived in Chicago. She was going home to Memphis. She was divorced with teenage kids. We talked about relationships, careers and travel experiences. Found out she lived no too far away from my hotel, I offered to give her a ride with the rental car.

She invited me in when we got to her house. Kids were with her ex. She kissed me as soon as we got inside the house. I did not check into the hotel until the next morning and had to rush to my morning business meeting.
 

Cbr20152012

Well-known member
Aug 7, 2023
425
830
93
This past Feb in a Chicago convention. Sat in the lounge reserved for special guests and volunteers with open bar and buffet. I was alone on a leather easy chair taking a load off my feet with a whisky after a long day. Slightly older lady was sitting across from me in a very nice skirt and suit jacket. People all around us, I caught her eye, we smiled. After 30 seconds I walked across and sat next to her and asked how her day went. 2-5 mins of commiseration and I put my hand on her knee and leaned in and we kissed. Never tried this before and I was shocked at my boldness. Suddenly she breaks away and said her co workers nearby might tattle on her so we went and found an empty meeting room and slid my hands up her skirt to a sopping wet pussy and proceeded to eat her out. It was so hot! Made plans later that night for drinks at her hotel lobby and spent the night.Best convention ever!
Gentlemen, this is the way (sorry - had to say it)…
 
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