Ok, so here is a quick background. A guy and I use to hook up often but we both moved away so have not seen each other for a few year's. Over the course of about 5 or so year's we got together about 3-5 times a month, we were both in our late teens and it was usually mutual oral and JO we never had anal. I have not been with a guy since. We have staying in contact via email, he is now married and I have a LT GF and we are both in our late 20's. Last week he emailed me and said he was coming to my area in a few weeks for a few days for business! I immediately wondered if he wanted to hook up again or was it past him now that he is married, I got the sense he felt the same so it took a few feeler emails out until we started talking about getting together, I am so excited. I have been craving cock for a while. We dropped hints about different things then it turned to fucking, he basically said he wants to fuck me, he was always the more aggressive of the two of us. I have no problem with his desire to do me. I have never been fucked but have wanted to and the fact it is someone I know makes it win-win. Considering I have played with his cock many times I know that is is on the smaller side, slight curve, maybe 5 inches hard which I think is good for anal, I don't want something as big as me (I am about 8 inches), a small cock should go in easier I assume.

So my question is any tips on getting ready for this? Should go buy a toy and start sticking it up there getting used to it? He basically said that the first day he arrives to spend the day and night just hooking up so I want to make sure I can handle it? During the act, any lube suggestions? Should I wear a thong or a jock so my cock isn't moving all over? Is dogging style better/easier of on my back?
Thanks

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Wear what you think he will like.Let nature take its course,and you might want to play with a toy just a tad before you hook up.No toy will replace the real thing .

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Hey guy

I think you'll enjoy your first anal experience more with a guy that's not too big, and especially with someone you know well; lucky you. I would definitely get some prior experience with some inanimate object, well lubed, before you have a guy penetrate you, to see how much you like anal stimulation and to get used to it. If you don't want to go get a toy you probably have plenty of smooth small penis-shaped objects around the house (even food--I was too shy to buy a toy in the early days).

I just did a yahoo search on anal sex tips and found a good article at about.com. I think you'd find it helpful. You want to be clean, not usually a big problem, and very well lubricated. Personally, I prefer silicone-based lubes because they are really slick, they last a long time and they are condom-safe.

Gentle, gentle, gentle. Plenty of gentle opening with a finger or tongue (both?) to loosen up. And plenty of foreplay to get into the mood, so that you're really relaxed and receptive. I think you'll have so much more fun because this guy is already somebody you like. Doggie is often the easiest for the top to get good penetration; bottom on top sitting onto hard dick is great for beginners because bottom controls entry; nothing like bottom on his back legs in the air for intimacy and the sensuality of looking into each others glazed, goony eyes.

And remember, it's your body. If you don't like it, you quit; there are plenty of ways of mutual pleasure. And even tho he's married, don't assume barebacking (no-condom fucking) is OK. You're responsible for your own health.

Hope you discover a lot of new erogenous zones out of this--have fun.

Fondly remembering my first getting-fucked....

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Good advice here...

Being a total top guy, this is my advice:

Make sure that you are perfectly clean. Anal douche is a simple and efficient way of avoiding a nasty surprise.

Use loads of lube.

Tell him to be patient and tell him that he is popping your cherry. He needs to know this, if he is a responsible top.

Use condom unconditionally.

Be prepared to take it like a man. A pain, discomfort and similar will probably occur. Most experienced bottom dudes will tell you that this is a small price to be paid for the pleasure.

Communicate. Do not assume that he knows, what makes you tick. Be inventive and offer to change positions, if you feel that you would do better in a different position.

Conventional wisdom says that you may want to try and sit on his dick for the starters and thus, control the speed of penetration. Maybe, this is a good idea.

OK, he is not the biggest of the dudes but you want to make it good for both of you. Even a 5 inch dick can and will hurt, if used without consideration.

Do not take it too seriously. Sex is mostly play. If it works, great. If it doesn't, try again.

KD

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I am FAR from an expert so take this with a grain of salt – but it is good that he is on the smaller side – most importantly hopefully he is thinner as well. It is not so much his length inside of you as his width opening your hole.

When I lost my cherry I knew my buddy had a big cock – but I did not realize at that age how much thicker he was that most. It was one hell of an adjustment!

Do make sure you are clean and make sure to wear a rubber – even if you both say you are safe it is only smart.

I am sure others will disagree with me on this part but suck him a lot to make sure you are both pretty far along because you want to have fun but you don’t want him to be pumping you for hours that first time.

Just make sure to go slow – and when you are know you have used more lube than you need USE MORE!

I hope all goes well – a couple years ago I got together with my old teenage sex buddy who is married – it was great fun but he felt real guilty after – it was the first and only time he cheated on his wife and although he had fun he still feels guilty.

- John

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Yea as a young twink all the older guys wanted to fuck my ass and first times were not that pleasant. With time and experience though it will come and feel so natural. I do recommend an anal enema to clean things out and make room for his meat and load.
I also think using a butt plug or dildo will open you up and esp the sphinter muscle which is probably still tight.
At first you should use lube and dont be afraid to sit on top of him and direct his cock into your hole slowly. Once the mushroom head gets in then slowly sit down and the rest will push in easily. Kissing and fondling are important at that moment and then start moving your bodies together in sync. Tell him how you feel and let yourself go. He'll be back for sure

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