Anal Connoisseurs

[Organicgrowth]

Gentlemen,

My head hangs low: mixed feelings, some positive some not so positive.

Firstly let me thank you all for the excellent suggestions. I think that last night was the longest period of time I have spent with a chica, for just one shot. It was also one of the most enjoyable sessions I have EVER had. We started at about 21:00 and were still “playing” at 0200, and I had not yet had a single shot.

The massage was what did it. I so enjoyed this that I just continued and continued. My chica actually asked me what had happened to me to make me so passionate! She came fully 2 times before I even made an attempt at her cherry. By this time I had an aching jaw!

The orgasms, massage and fingering had done their trick. She begged me to go for her third hole and I just had to try! The easiest position was with me next to her, but behind (like spoons…). She helped by opening her buttocks. This was excellent because I could then use my hands to get some controlled fingering, extra lube and off course help the slide-in.

We made some real effort, but I only managed to get the head in. Once it was in, I just stayed still and let her get used to it. She said it was a little uncomfortable but not painful and so she would not push into me. Also I decided that having got the head in, if I pushed too hard, she would be in pain and that would end the whole thing.

Using my free hands, and with just my head inside her arse, I inserted a few fingers into her from the front and at the same time played piano on her clit. When she burst into orgasm for the third time I thought the tightening of her arse was going to rip my dickhead off! It was fantastic. While she was moaning I tried to push forward and into her, but the tightness was so powerful I did not get deep.

One thing I will say at this point: I’m not claiming this cherry yet. I want another inch of penetration, maybe more, before I can honourably say its my cherry.

I have to tell you that the condom made the penetration difficult, even though I had a LOT of lube. My dick was moving inside the condom, and the masses of lube, made control difficult against a tight arse. With pre-broken chicas there is no problem as we can just slide in and move all we like. I’m finding that breaking this cherry needs more movement control.

I’m seeing her next week again and we have agreed to try it. She wants more massage and more fingering! By next weekend I will have managed to get a vibrator and so the next step will begin next Saturday. I will report back.

THANK YOU ALL for getting me this far. Please keep your suggestions coming.

Regards Havanaman

[Lazzaro]

Psychologically I love the idea of massage, thanks Lazzaro, but the physical idea of using fingers, one at a time like BootyLover says is I think excellent. Also the idea of plugs as suggested by Sterling V makes sense and means we can enjoy a bit of 69 in the process.

Is using a small vibrator, very well lubed, perhaps too much because of the vibrations: what do you think? I don’t want to put her off. At the moment she is really wanting it and that is a rarity for any non pay-for-play chica I have been with. So much to think about (and enjoy!). Saturday night is the big night! I will keep you posted.

Everyone of us have a personal strategy.....
Yes I know that in my way it takes a lot of time, but for the esteemators, the long time which drive you to a total exciting is a part of.
You could do a sort of mix of them: good short massage (to relax) and fingers. Why don't combined?

For the small vibrator, IMHO is an excellent idea. If used well, the vibration could give her a sort of orgasm.

I'm waiting for read your report.
We're all on your side!!!!!



Ciaoooooo

[Organicgrowth]

Gentlemen,

I feel honoured that so many of you have either public posted or PM’d me your collective wisdom. I like all the ideas I’m reading and will try them. It would seem that patience is the main consideration as suggested by Badass.

Psychologically I love the idea of massage, thanks Lazzaro, but the physical idea of using fingers, one at a time like BootyLover says is I think excellent. Also the idea of plugs as suggested by Sterling V makes sense and means we can enjoy a bit of 69 in the process.

Is using a small vibrator, very well lubed, perhaps too much because of the vibrations: what do you think? I don’t want to put her off. At the moment she is really wanting it and that is a rarity for any non pay-for-play chica I have been with. So much to think about (and enjoy!). Saturday night is the big night! I will keep you posted.

Thank you once again Gentlemen.

Regards, Havanaman

[BootyLover]

From experienced ass diggers like you, I have been expecting more specific advice. I have taught many girls into this. Here my way:
1- Compare your dick diameter to your finger and find out how many fingers compare to it

2- With too much lube start with one finger a reach the number of finger you found in 1. P.S. (I you have a really big dick forget anal from common girl)

3- With more lube, put your dick against the sphincter, have her push out, push in one third of your dick and stop moving

4- Ask her and when she feels okay start moving slowly and short range
5- when she ask for it go as deep as posible and you are done.

P.S. Never try it doggy style the first time

[Opebo]

The anecdote about the difficulties of first penetration reminded me - I hate to be the first one! Due to certain atypical dimensions I'm a bad candidate for breaking a girl in. I like a girl who's very experienced, who's ass is really open. Or as I like to put it 'sprung'. You know when it is so open you can look at it before you even start and it looks like its been through a lot. Then, after you've popped it open and stroked in and out a bit, it gapes open lewdly. The best is when they just hang open the whole time.

Then again I guess I'm unusual in preferring the trashiest, most well broken in ones. The last thing I want is some reluctant young new one who can't handle a deep dicking.

[Vegamars]

In this way slowly and slowly I think it's gonna take about 80 years to reach the end,anyway better than never!!

[Lazzaro]

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I’ve been seeing this incredible chica recently and she wants her third hole opening. Man have I tried everything! Fingers go in OK, no problem. When it comes to Mr. Happy, not a millimetre. Using good quality lube, a number of positions, tried before and after her having an orgasm, relaxed atmosphere, nothing seems to work... Your advice most appreciated in helping me get my first Arse cherry. Please note I only do covered.
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I found myself in this position.
The only thing I can suggest you is to be paaaaaatient!
...and (if she want/try) let her do with you what you do with her...

We began to play each other caressing each other, kissing, ....
It's for slide in the excitement.
Than I started with a slow, long, sweet massage on her back.
With a oil/cream it is better.
Than, very slowly, I began to massage her legs (yes I jumped her cheeks - for the moment) and after awhile I do it on her cheeks, letting "slide in" sometime (quite by accident) the thumb, never stopping the massage.
It took about 20/30 min. when, with my hands totally oiled, I started to play with the hole, inserting sloooowly only the top of the finger, (remember never stop the massage and never stop to kiss her back/cheek).
After awhile she wanted to do the same with me, so I let her try in a sort of "69" position.
When I achieved to insert deep all the first finger, I started to play with the second finger lettting the first inside.
All the movements must be "circular": it means you have to rotate the finger all along the perimeter of the anus.
When you could play with two finger, you could begin to "oil" Mr.Happy (I think that at this time he will stand very proud) and lean it at the hole with a little press.
Let it slide in very slowly and when you have inserted it a little bit, stop and watch her face and regulate yourself lokking her faces.

I did so and we had a very good time.
Keep in mind: I did so, but I don't say it is the right way. With me it worked (and works right now!) but every girl is soooo different....

Last thing: I think that if anal is choosen in freedom from both the partner (also if it liked to both), and it is part of the sexual relationship/game/games, you both could have one of the best moment of sex of your life.

This is my 5c of report

[Bizzie]

I’ve been seeing this incredible chica recently and she wants her third hole opening. Man have I tried everything! Fingers go in OK, no problem. When it comes to Mr. Happy, not a millimetre. Using good quality lube, a number of positions, tried before and after her having an orgasm, relaxed atmosphere, nothing seems to work... Your advice most appreciated in helping me get my first Arse cherry. Please note I only do covered.

Advice:
1. Go sloooow. It has taken me weeks/ months to get it going sometimes. That is after she was willign to try!

2. If she has pain, she'll be turned off to it forever, and you won't get your cherry.

3. No amount of lube is too much.

4. Fingers do not fit the hole naturally. Try dildos/vibrators shaped like a penis .

5. Most importantly, have her insert the toy HERSELF a few times. She'll learn to relax with the penetration.

In the end, you've got to be patient!
If she gets spooked, it's over

[Sterling V]

Try using butt plugs. Start with a small one, leave it in for 10 minutes, move up to a larger size, 10 more minutes, and so on. Giving and/or getting some head during this time is always a good way to pass the minutes.

[Organicgrowth]

Gentlemen,

OK, here goes...

Like many a normal man I’ve enjoyed every female penetrable hole going, regular and pay for play. Now I need some advice. I’ve taken a number of vaginal cherries in my time, but never broken an arse myself. I’ve always had them pre-done…

I’ve been seeing this incredible chica recently and she wants her third hole opening. Man have I tried everything! Fingers go in OK, no problem. When it comes to Mr. Happy, not a millimetre. Using good quality lube, a number of positions, tried before and after her having an orgasm, relaxed atmosphere, nothing seems to work... Your advice most appreciated in helping me get my first Arse cherry. Please note I only do covered.

Regards, Havanaman

[Raider]

ProKofiev yes this was in Dallas .Thanks for the advice on the lube .I thought that it was Vaseline but I could be wrong as the lube had a blue top and yellow tube I asumed it was vaseline.I will be more careful next time around.

Also Alan I now this sounds too good to be true but amazing things happen .I understand what you were saying though she looked tight she really wasn't after I penetrated and I went in easily as the Gal was experianced in Anal sex and had done it many times before and that is why I could go in all the way and do her in different positions .But thats my side of it and you are welcome to your opinion.

She called me today and I am meeting with her again in a few hours so I will post if anything spectacular happens .

Thanks all for your input .

On Deck

[Alan]

Friends,

On Deck has been reading too many pornographic stories. Vaseline will break down the latex in a flash and cause your cock to come into full contact with the girl's hiv-infected rectum. Also, you clearly could not have gone "balls deep" in the kind of tight rectum you have described. I wonder how many veterans out there have been able to go all the way in even with real pros.

Sounds like good material for a porno movie though. Sell the idea to Seymore Butts. But spare us who have been there and done that.

[Prokofiev]

On Deck,

That sounds too good to be true. In the USA? Congrats . . .

-but was it really Vaseline she used? Bad idea. Oil based lubes can destroy latex. Must use water based lubes for safety. Both yours and especially hers.

Cheers, -P

[Raider]

I finally found a gal who does did the whole nine yards .I had full penetration anal sex with her (with lube and condom of course).She is a wsw who I had come across a long time ago and hadn't seen her out in a while And on one of my recent quests for pleasure I seen her again and took her to my favourite motel and she liked the room with the built in Jacuzzi/tub she asked if she could stay longer .I had some chilled beers in the cooler and offered her some .We got to talking and I told her about my fantasy and how though I had had anal sex I hadn't had the perfect one as yet.She was really into it and told me that tonight was the night she would make it come true .Let me describe her first ,she's petite about 100-110 Lbs,brunette,smallest pair of titties I have ever held ,nice size light brown nipples ,she's 22 years old and has green eye's.

We got into the Jacuzzi together after a shower and are drinking our beers and relaxing when she comes over to me and gives me DF Kissing and starts playing with my dick. In a few moments she asks me to get out of the tub and sit on the edge with my legs spread and she goes on all fours and deeps throats me almost to the point of her gagging ,but she gets used to it and keeps giving me great head.She then grabs my dick and goes down licking and sucking my balls and goes all the way down to my anus and starts licking on it .I can't tell you how good that felt she then got back to the bbbj and went to and fro from my dick to ass.It felt so food that I had to come I couldn't control it anymore and told her I was about to come.She then started sucking my dick in slow rhythmic motion and I blew my load into her open mouth. After I was done she licked my dick clean of the last drops of come that came out and swallowed the whole load. Wow! that sure felt nice even though I have had it done before.

We then proceeded to the bed and we relaxing and watching the TV and after some time she slides her hand down and starts to get me exited all over again. Once I was ready after another good dick sucking that she gave me. She pulled out a tube of Vaseline and put it on the condom she slipped on and put some on her ass too. She then went and all fours and asked me to go for it. Seeing her small ass and tight pink hole I was afraid my dick would never go in. To my amazement when I put my tip on her asshole and pushed it slid in so easily and in moments I had pushed my dick right up to my balls all the way in.I then Fucked her doggy for a while, then we switched to her on her back and her legs on my shoulders I could see her face in front of me and my dick goin in and out all the way, What a turn on ! She said to me that I could do her harder and faster as she liked it that way and I then really fucked her ass like I would a pussy. And she moaned with pleasure as I fucked her hard and fast in her ass. I then got her to lie on her stomach and fucked her from behind and it was a great feelin.She also later asked me to sit up on the bed and rode me cowgirl and reverse CG it was awesome. I finally was about to come when I told her to get back onto her back and I did her missionary position in her ass and blew my second load into her ass. This was byfar the best anal experiance I have ever had and it cost next to nothing. I gave her 60 bucks for 2 hours we spent together.I will definately be seeing her again soon.I gave her my tel numbers as she did not have any contact number.And asked her to call me up every week.

On Deck

[BootyLover]

Unless your're chasing on low bucks (car, walking, in hurry, etc.) the best way to find a clean ass is a mutual shower where you finger the ass with soap to clean it. Otherwise, analingus may be out of reach.

Everything has a price. Anal lovers will be called gays by some women, this is one price to pay, another would be to have some lube handy for every sexual encounter. I justify it a way to protect my condom against breakage due to excessive friction (true). In fact, my primary reason is an ass-pectation