Obsession Massage

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

FunAndGames

New member
Nov 8, 2013
27
0
1
The girlfriend and I were in our early 20s, both really wanted to give it a try. She was terrified it would hurt, so first we get completely shit-faced (so to speak), then she slathered me with half a jumbo tube of K-Y. Then I grabbed the tube, and emptied the rest of it lubing her up, inside and out. So we're all set, she gets on all fours and grits her teeth, bracing for that holy-god-I'm-being-torn-in-half agony. Well, we'd used so much excessive that lube I slid into her before she knew what was happening, and she turned to me a few seconds later with the dreaded words all men fear:
"Are you in yet?"
At which point I started laughing uncontrollably and, well, the experiment was over.
 

bobistheowl

New member
Jul 12, 2003
4,403
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Toronto
Um..but first you have to pull it out!!:Eek:
Technically speaking, if you're with an Escort, you'll have to pull it out before you can pull it out, pull it on, push it in, pull it out, push it in, push it out, and pull it out. At a MP, however, you pull it out, then you pull it out, then she pulls it out.
 
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Ceiling Cat

Well-known member
Feb 25, 2009
29,142
1,845
113
In my 20s, I knew a girl from Dundee ( Scotland ). She had tried anal but she said it was too painful for her, my guess is that most guys are in too much of a hurry and just want to shove it in. I took my time and made sure to use lube. Some girls can only take short strokes. I have met other girls that have such a loose butt hole that I have just walked right up and slid it right in without even using my hand to guide it in. The best sex I ever had was with a girl that was really into anal, she enjoyed it as much as I did. When I cum, she would squeeze her butt muscles and grind her ass in a circular motion and drain every drop out.
 
My first was with an SP that offers it to all and loves it from what I can tell. Unfortunately, it was such a focus to her that it didn't really work for me. It was my first time with this SP and we really didn't connect, which didn't help the matter. Every time she tried to urge me to try, I'd lose it and wouldn't be hard enough to even try. My second experience was much better. It was a favorite SP . She only offers selectively as she is very small. We had been seeing each other for some time but although I knew it was offered and had talked about it, we never tried it until one day, she brought it up that she wanted to try. I could tell she had planned it which was nice. It was great actually but again, because of the way it came up, I didn't find it that exciting. Now, several months later, I was in doggie position with this same SP and for some reason, I was in the moment and asked for anal. I was eagerly accepted. Now that was the best!
 

Mr Deeds

Muff Diver Extraordinaire
Mar 10, 2013
6,546
3,822
113
Here
I never understood the attraction to it. Does nothing for me
 

Ridgeman08

50 Shades of AJ
Nov 28, 2008
4,492
2
38
I freaked out because I liked it too much. And one particular position is still my absolute favourite.
FINALLY! A worthy authority on the subject! Thanks for chiming in Kat!

Sophia?

SexySpinner?

Laura?

Amber?

Anyone else?
 

anonymong

Active member
Jan 27, 2010
858
147
43
Toronto
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.
Oh man, that one sentence sounds sexy as hell! French lady in her 60s ... I'm picturing someone with a Catherine Deneueve-like vibe ... just enjoying making love in all positions ... whew!!
 

foxxxy lady

Amber aka Jessica Rabbit Foxxxy Lady
Oct 12, 2009
4,486
4,458
113
Durham Region/ Toronto
FINALLY! A worthy authority on the subject! Thanks for chiming in Kat!

Sophia?

SexySpinner?

Laura?

Amber?

Anyone else?
http://foxxxylady.callgirlfiles.com/home










I cannot ignore the invitation, xo. My first experience with anal was horrible I was riding up and down on my boyfriend who moved me a little and it went right up my ass. Now I think I my know what it feels like when a guy gets kicked in the balls the pain went rightt into my stomach and through my entire body so needless to say it was a good ten years before I attempted it again. Watching porno in some of the clubs I was working in stirred up my interest again, It looked like it was fun and the girls and guys in the porn were liking it, so thanks to Google I read up on the subject. I also had a great conversation with my doctor, I asked him all kinds of questions like will I have to wear diapers in a few years, will it stretch out my hole etc. etc. I think we chatted for a good twenty minutes on the subject after being convinced these were myths(u should of seen the people in the waiting room faces my voice is a little loud sometimes especially if im passionate about something omg.) I decided I wanted to try again and I'm glad I did;)

Now my favorate position is having my legs up in the air so the guy can see my pink pudgy pussy at the same time and I can rub my clit, (its feels great for me and for the homophobic kinda guy he knows its a chic who he has his cock in the ass with.

I am a human and do train so I eat six small meals aday so ,a few times not by choice ther has been a little mess on the condom, but I take it off right away tell the guy to hop in the shower and I wash my ass till it is squeaky clean. Usually the condom cums out clean as a whistle, whew

I lube my ass well o rbetter yet I get the guy to do it, really they don't mind

I do hours so I do msog, I like anal on the first shot when the cock is at its hardest.

I have no complaints about anal sex at all it is very pleasurable. I even bought a Spartan type dress lately, just for fun

It may not be for everyone I never force a guy into it we all have our likes and dislikes

xo amber
 
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bridgette_xo

Member
Oct 21, 2011
384
3
18
Toronto
www.sweetbridgette.com
My first time trying anal was on prom night with my boyfriend at the time. We had had a few drinks and were fooling around for a long time already when he asked if I minded. For some reason, I just said sure and we tried it. It slid right in but felt strange. I let him try it for a bit before saying I wasn't sure that I liked it.

After that, I once had a boyfriend accidentally "slip" out of the V and into my bum. That REALLY hurt and turned me off the idea of anal, especially while I was writhing around in agony!

Then, I had very long term relationship with someone I would consider to have an ass fetish. We tried anal and prepared and researched prior. It was a much more enjoyable experience for me. I learned to cum from anal too!

Now, I will do it if I'm very horny and other options are limited. My biggest problem is it makes me cum TOO fast and I'm done and my partner isn't! I find after I cum it begins to hurt sometimes.

Please note that although I have expressed my input in this thread, Greek is not something I offer in my services.
 
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HAMSTER INSPECTOR

Well-known member
Jun 3, 2005
1,745
41
48
I have done anal many times without incident and I really enjoyed it. You still have to be careful. If you go into the woods, you may meet up with a bear. There was one occasion where I was pumping the back door and the girl was moaning the whole time. When she got up to go to the bathroom, she took two steps stopped and dove for a waste paper basket and made a deposit. You always have to use lube, but you can use too much lube. On another occasion I was pulling in and out of a well lubed butt, what I was really doing was pumping air into her ass. When I was done, she let out a huge QUACK sound from her ass and shot a half a tube of lube out like a sneeze all over my groin. Sometimes doing anal you pull out a poopsickle, One time I pulled out a condom that was covered in pudding, i was astonished. The girl just grabbed the condom by the shitty tip and pulled it off with a snap noise sending specks of pudding on to her bare skin. She cleaned up without freaking like I did.
 

Ridgeman08

50 Shades of AJ
Nov 28, 2008
4,492
2
38
I cannot ignore the invitation, xo.
Thanks! NOw, we're getting somewhere!
I do hours so I do msog, I like anal on the first shot when the cock is at its hardest.
Yes! I remember it well!

I have no complaints about anal sex at all it is very pleasurable. I even bought a Spartan type dress lately, just for fun

It may not be for everyone I never force a guy into it we all have our likes and dislikes

xo amber
Like I said earlier, if done properly, it can be a very pleasurable experience for both the giver and the rec'ver! ;)
 

Dougal Short

Exposed Member
May 20, 2009
1,227
18
38
I My first experience with anal was horrible I was riding up and down on my boyfriend who moved me a little and it went right up my ass. Now I think I my know what it feels like when a guy gets kicked in the balls the pain went rightt into my stomach and through my entire body so needless to say it was a good ten years before I attempted it again.
This reminds me of my first, and last (for about 30 years) experience with tequila!

I have known two "professional" ladies that LOVED it... and so I loved it with them. Any other experiences were awkward or painful so it wasn't enjoyable for either of us...

When it's "good" though... It's amazing it seems.

I don't recall any civilian lady that I would say "loved" it. The ones that seemed to enjoy it were drunk... ;)

INow my favorate position is having my legs up in the air so the guy can see my pink pudgy pussy ... for the homophobic kinda guy he knows its a chic who he has his cock in the ass with.
LMAO... Ya, I bet that happens a lot eh? Guys suddenly think they're with a gay guy??? WTF? Not likely...
 

foxxxy lady

Amber aka Jessica Rabbit Foxxxy Lady
Oct 12, 2009
4,486
4,458
113
Durham Region/ Toronto
This reminds me of my first, and last (for about 30 years) experience with tequila!

I have known two "professional" ladies that LOVED it... and so I loved it with them. Any other experiences were awkward or painful so it wasn't enjoyable for either of us...

When it's "good" though... It's amazing it seems.

I don't recall any civilian lady that I would say "loved" it. The ones that seemed to enjoy it were drunk... ;)




LMAO... Ya, I bet that happens a lot eh? Guys suddenly think they're with a gay guy??? WTF? Not likely...
not all guys sir, however I have met a few who are uncomfortable with the ass, I am not saying all men,(or you), trust me when the pie is in the sky, they are all good with it, just my experience . I cannot speak for all the sober civilians (im an escort not a cop) out there, however being sober and a civilian myself I love it

xo amber


http://foxxxylady.callgirlfiles.com/home
 

Ridgeman08

50 Shades of AJ
Nov 28, 2008
4,492
2
38
Then, I had very long term relationship with someone I would consider to have an ass fetish. We tried anal and prepared and researched prior. It was a much more enjoyable experience for me.
The 4 P's... planning, preparation and patience= pleasure!

I learned to cum from anal too!
Now we're talking! I've been on the rec'ving end of a number of assgasms by a number of ladies. (I may have even written about several of them... ;) :D) It is truly an experience to behold! Incredible how the muscles inside contract, inducing my own uncontrollable orgasm! I love it!

Now, I will do it if I'm very horny...
Note to self...

My biggest problem is it makes me cum TOO fast
I fail to see how that's a problem... See above...
 
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