Garden of Eden Escorts

Anal sex : How difficult was your first entry? Good experiences? Bad experiences?

Sep 13, 2009
564
16
18
I tried maybe about 10 times before I was able to make entry. Sometimes I would use to much lube and the sausage was sliding all over the place and sometimes entry was just not possible. My first successful entry I just slid it right in and it was only the last inch where I got a gasp from the lady. Slow gentle humping is the way to go, no too many girls like it when you make the wop wop noise like in the porn films. There were a few times where there should have been an ocupado sign on her ass before I made entry. What are your experiences like?
 

asterwald

Active member
Dec 11, 2010
2,579
0
36
It was painful. I almost cried and the SP apologized to me.
My cock felt like it was being strangled. Very painful.

But later I tried again with another provider who knew how to lube up properly, it was ok.
 

TeasePlease

Cockasian Brother
Aug 3, 2010
7,732
5
38
My first time down the hershey highway?

It was shitty.
 

The Searcher

Member
Jan 30, 2014
590
2
18
I never tried it but I have been very curious to know what it's like. Maybe one day
 

GameBoy27

Well-known member
Nov 23, 2004
13,056
3,093
113
My first anal experience was with a 11 year old girl. Now before you get your panties in a knot, I was the same age. Her parents were out and we did it on her washroom floor. She was really tight so we used some Vaseline which helped a bit. Now, the reason I went for anal is because I didn't know out about the vagina until we were playing doctor a few months later. lol
 

TeasePlease

Cockasian Brother
Aug 3, 2010
7,732
5
38
My first anal experience was with a 11 year old girl. Now before you get your panties in a knot, I was the same age. Her parents were out and we did it on her washroom floor. She was really tight so we used some Vaseline which helped a bit. Now, the reason I went for anal is because I didn't know out about the vagina until we were playing doctor a few months later. lol

Hey bud, that playdate we had scheduled between our kids? Sorry, it's cancelled. LOL.
 

IM469

Well-known member
Jul 5, 2012
11,147
2,505
113
I never gave it much thought partially because I'm a little bigger and I hate the look and smell of shit so keeping the door closed was my preference.

I was dating a small cute Japanese girl who was into rough sex and one time as I was doing her doggie when she took my dick and put it onto her butthole. I worked slowly and soon I was half in. It was an unexpected pleasure not only for the tight feeling but the visual of this tight little ass with my dick in her. That was my first time, I have enjoyed a few times since but I much prefer the other gateways to bliss.
 

mandrill

monkey
Aug 23, 2001
80,256
104,570
113
I got pooped on twice.
 

xmontrealer

Well-known member
May 23, 2005
10,487
8,110
113
My first time anal we were having regular sex. At one point we switched to "puppy style", and by mistake I put it in her pooper. (I guess it wasn't her first time at anal, as it felt pretty much the same as her vagina, and she didn't give me any indication that I had switched holes!)

I was quite young and did not realize the difference, until a minute or so later when I put my hand underneath her to play with her clit, and found that I wasn't in her vagina.

It dawned on me that I was in her ass, and I came within 2 seconds! (I think my brain exploded at the same time!)

Later we had a good laugh about it.
 

pokergod

Member
Apr 15, 2007
614
0
16
I've done it a few times. I've always wanted to try it from watching porn. I talked her into trying it and it took a long time to do so. We lubed it up real good and she could only do it CG. She did ok and said it didn't do anything for her. The next few times, she was nice enough to use that hole since it was the time of the month. The last time we did it and the final time, I came up her ass and she did not like that feeling of the cum dripping out of her ass. Yes this was bareback but with my GF of 7 years.
 

bobistheowl

New member
Jul 12, 2003
4,403
3
0
Toronto
About 1994, with an Escort named "Kiki" at that time. I found her from Red Zone voice ads. Her name and location would change every 6-9 months, but it really was her voice on the ad. She was "Sierra" for quite a while, based in Mississauga.

She had incalls at a condo on Jarvis, just south of Bloor. I remember she had a hot tub in the living room, and cheap porno was playing on VHS cassette on her TV. She could deep throat, but it was CBJ. We were all sweaty after being in the hot tub. I REALLY enjoy it when a woman is very sweaty during sex, even though I usually don't perspire much myself.

I guess I did a yeoman's work on DATY, so she decided to 'reward me'; Greek service was not mentioned in her ad. Anyway, she got on all fours, and I got ready to enter her doggie, and she said: "No, higher!", and slid me in. I originally thought that my aim had been off, since I wasn't wearing my glasses, and it didn't dawn on me that I was in the other place for about five minutes, but when I clued in, I didn't last a whole lot longer.
 

bobistheowl

New member
Jul 12, 2003
4,403
3
0
Toronto
I've done it a few times. I've always wanted to try it from watching porn. I talked her into trying it and it took a long time to do so. We lubed it up real good and she could only do it CG. She did ok and said it didn't do anything for her. The next few times, she was nice enough to use that hole since it was the time of the month. The last time we did it and the final time, I came up her ass and she did not like that feeling of the cum dripping out of her ass. Yes this was bareback but with my GF of 7 years.
I was taught that a gentleman should always push in a woman's stool.
 

Terminax

Member
Sep 30, 2008
222
3
18
First time was in my early 20s, awkward, and not very fun for either of us. Wasn't a problem of lube or anything, just inexperience on both our parts. One of my more recent ex's, a french lady in her 60s often used her hand to slip me out out her pussy and into her ass when she was particularly horny then ride me reverse cowgirl until I got off.
 

Ridgeman08

50 Shades of AJ
Nov 28, 2008
4,492
2
38
I touched on this subject recently in another thread...

There are 3 golden "P" Rule's that need to be followed whenever a tour the islands takes place!

Planning, Preparation and Patience!

If there is any pain... you're doing it wrong.

If there is any "mess", you're doing it wrong. (Or she was not properly "prepared")

If you follow those P's, you will both be rewarded with the forth "P"!

PLEASURE!
 

legmann

Well-known member
Dec 2, 2001
8,749
1,365
113
T.O.
I tried maybe about 10 times before I was able to make entry. Sometimes I would use to much lube and the sausage was sliding all over the place and sometimes entry was just not possible. My first successful entry I just slid it right in and it was only the last inch where I got a gasp from the lady. Slow gentle humping is the way to go, no too many girls like it when you make the wop wop noise like in the porn films. There were a few times where there should have been an ocupado sign on her ass before I made entry. What are your experiences like?
Once you've done it, it really is no big deal; it's just another sex act, not some unattainable grail. With the right girl - experienced, and ideally horny - it shouldn't be difficult at all and will be no different than vaginal.

Initial penetration takes longer in some cases than others, but once in and her sphincter relaxed, you will be amazed at how easily you can reinsert after sliding all the way out.

If you're not able to penetrate at all: you're either way too big, she isn't relaxed enough, or is apprehensive to begin with.
As I've said before, with many girls, sheer desire for is going to trump anything else - if she really wants it, she will fit you in - lube or no lube.

For your first time: how 'enjoyable' it is, is very likely going to depend on who you do it with.
 
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