Hoping to get f-cked for the first time on Friday... Any advice?

[Yankee]

I have an appointment tomorrow with an escort (who is well reviewed in NYC) and I just told him that I have never had sex with a guy before. Embarrassed to admit that my wife has hated sex for all 14 years of our marriage, and I only learned about these sites in December, so I only now got the courage to see what sex would be like with a guy. Sounds crazy that a 46 yr old can be virgin, but it's now a problem. Two weeks ago, I posted that I was looking for a dominant verbal guy and people suggested a guy from Vegas that was dominant and very verbal but that he would be too punishing for me to let him do anal for my first time. So, I just did oral with him and it was great. Now, I have set up a meeting with a guy who is verbal, but I heard he can also be gentle. So I think he should be my first. A few days ago, I used water based lube and put my finger in, and it didn't hurt, but I'm really worried that anything bigger will. Going out shortly to get a stiffer dildo after stupidly buying a dildo last week that is too squishy and floppy. Any advice? I've learned how to clean out, but anything else I need to know that can help me get past fear of pain? I'm POSITIVE I want to do this. Do I tell the escort i'm afraid? I'm willing to pay for 3 hours even if this only takes 1 hour. I booked 2 hours, but I just want to get past the virgin stage so I can get on with seeing if i'm going to enjoy getting f-cked in the future. Thanks guys, Yankee

[Alec Andrews]

Congrats on your new adventure.

 

#1. Skip the water based and move directly to silicone based lube. While tough on the sheets, it's easy on the hole and will help you not get a possible hemorrhoid.

#2. Practice first. Get a dildo, learn to mentally release and let go. This will help. This is almost an entire mental game.

#3. Pick a "normal" sized 7in guy who is well-reviewed. You can upgrade with more experience. In this instance its not the size of the ship but the motion of the ocean that counts.

#4. Fear is pointless. This is an exciting adventure. The prostate is OUR FRIEND and a beautiful manly gift. Be Excited and you will feel amazing.

#5. Just see him for an hour. Anything more and you are wasting your hard earned money. More than an hour is for an emotional connection. What you need is a firm cocked man to take control, force you to submit and show you what pleasure really is.

 

Go get it boy.

[Jon Royce]

I agree with everything Alex wrote above, and have two personal additions.

1. As you mentioned clean your hole out until it is squeaky clean. It really helps and pre-lube if you can with a dildo afterwards; and

2. For me personally, being able to smell the top's armpits helps. I don't know why, but it does. For example, if Alex above were banging me (note to self - make it happen) while I was on my back, I'd find a way to sniff his armpits. If Alex had me on my stomach, I'd find a way to get a sniff.

Good luck and let us know how it goes.

[m4hotness]

I hope you have a great time! I have a fear of the pain too as I haven't bottomed much in last 5 years. One terrific guy that I hired for an overnight, was very good at eliminating the pain. He can travel to you. Not going to put his name here cause I don't want it to sound like a review. Pm me for details.

[+ Gar1eth]

I'm sure Alec has a lot experience with initiating anal virgins. But -and I'm a top here (my prostate is definitely not my friend-but I realize not everyone has my medical issues)-I think I have to disagree on the only schedule for one hour. You are going to want to get comfortable with the environment, the situation, and the escort. I think 2 hours is probably a good amount of time. You don't want to be rushed.

 

As for the escort-yes you need to tell him that this is going to be your second time with an escort and first time bottoming. And I'd tell him before you meet. I really wish you were in LA-I know Alec is a responsible experienced guy who'd be great for a first timer. So I hope you did pick someone experienced and empathetic. It should be an escort who is more concerned with your feelings and not his own.

 

As for being a virgin at 46-the first time I had any sex whatsoever I was 41. I had never even Fr kissed anyone. The escort had to teach me how to kiss. So don't feel bad. You at least have had intimate relations going into this.

 

I wish you the best.

 

Gman

[+ Gar1eth]

PS Remember to play safe.

 

 

Gman

[wisconsinguy]

Congrats on your new adventure.

 

#1. Skip the water based and move directly to silicone based lube. While tough on the sheets, it's easy on the hole and will help you not get a possible hemorrhoid.

#2. Practice first. Get a dildo, learn to mentally release and let go. This will help. This is almost an entire mental game.

#3. Pick a "normal" sized 7in guy who is well-reviewed. You can upgrade with more experience. In this instance its not the size of the ship but the motion of the ocean that counts.

#4. Fear is pointless. This is an exciting adventure. The prostate is OUR FRIEND and a beautiful manly gift. Be Excited and you will feel amazing.

#5. Just see him for an hour. Anything more and you are wasting your hard earned money. More than an hour is for an emotional connection. What you need is a firm cocked man to take control, force you to submit and show you what pleasure really is.

 

Go get it boy.

Yankee, welcome to your new adventure! I started my "new life" a little over a year ago. So I consider myself a newbie in many ways. However, there are friends on the forum that were more than happy to help me "explore." There were so many members that had fun and logical advice. I had so many simple questions that caused me anxiety that I spent months in the bathroom either puking or pooping. So, there was no doubt I was clean! Once I made my decision, and based on recommendations from this group, and called my selection. I was honest, explained that I was a "virgin" and not even kissed a guy. He said not to worry, we would have fun, both in "playtime" and other extra time. I spent an extended weekend with him.

It was the one piece of advice I digressed from. I made that decision, and never looked back. If you have the funds, I would recommend 2 or 3 hrs. It gives you time to explore and enjoy and experience many firsts.! I still see that first person exclusively. He provides me with many firsts. He knows about me, the good and bad. He has shared his life with me. I am proud to call him a friend. My final comment is, sit back and enjoy. Let your person know know he is in control. If you r honest with newness, he should be able to provide u with a fun, sex filled time! Oh,it does hurt a bit. But,

once he is in your cockpit, let go!!!

[BaronArtz]

Congratulations with your new adventure. It could be the beginning of a whole new life for you! You have received excellent advice here. One thing I could add is: bring a lidocaine ointment with you. It will numb the initial pain if this is something you may be worried about. Discuss it with your escort though. Above all, enjoy!

[TruHart1]

Congrats on your new adventure...

 

[instructions 1. thru 5.] etc...

 

Go get it boy.

 

Alec's expertise in this area is truly phenomenal!!! Still, I agree with Gman that a couple of hours might be better for a virgin experience, so you can adjust your mental & emotional state and not feel hurried!

 

Stay safe, be sure he uses a condom and enjoy your first time, it only occurs once!

 

TruHart1

[Kenny]

A.) Tell him it's your first time. B.) Deep exhale during entry. It'll help your body r-e-l-a-x.

[loverboy95]

One thing I would like to say is don't freak out if during the process or after it's over, you find that it didn't go as smoothly as you hoped. If it is awkward the first time, it is natural and has happened to everyone at one point. I do hope that this is someone special whom you will remember!

[+ azdr0710]

if not already obvious, communicate with your guy!.....before the meet and during.....slow and easy....two hours is good.....rushing is no good!

[BabyBoomer]

I sent you a PM.

 

~ Boomer ~

[gallahadesquire]

+1 for all the above. And as a general rule in life: If it doesn't work, it's not a failure; it's just an experience. Don't take it as a personal insult.

[+ Gar1eth]

Congratulations with your new adventure. It could be the beginning of a whole new life for you! You have received excellent advice here. One thing I could add is: bring a lidocaine ointment with you. It will numb the initial pain if this is something you may be worried about. Discuss it with your escort though. Above all, enjoy!

 

I was thinking about suggesting lidocaine. But the 2% (and probably the 1% is too) is by prescription only as far as I know. And you need to make sure you don't have any heart problems although most likely you wouldnt absorb enough to cause problems.

 

This actually brings up a good point though. I'd say it's essential to have a healthcare provider you can trust about gay issues. I'm not saying you have to tell them you are meeting an escort. But you want someone that you can have discussions about gay sex, and is up on what regular testing you should receive- for example- HPV, Hepatitis A, and Meningococcal Menningitis Vacccines are probably not out of line. Oral throat and anal swabs along with urine tests for gonorrhea and chlamydia -every 6 months to a year-HIV testing every 3 to 4 months or so (depending on how active someone is), and maybe Herpes antibody testing every couple of years. I'm not saying your general family practitioner or internist couldn't do these things. But if they dint have a lot of gay patients, they may not think of all this.

 

Gman

[rvwnsd]

I agree with everything Alec says with one exception: the lube. I do not like silicon-based lube. That's just my preference, but if I was in your position and had silicon-based lube I would also have water-based just in case. I suggest H2O JO. I also suggest using polyurethane condoms. I find they feel better than the latex ones.

 

Jon and I have something in common: a love of armpits. A fella I've hired a couple of times has wonderful armpits. Takes fucking to a whole new level.

 

Lastly: While I agree with Alec on the one-hour session for your first time, you could ask your guy if he is open to planning on an hour with the option to extend to two hours. That way, if you are "done" after an hour you can be done in an hour. If you are up for more time, then you can have more time.

 

Alec is a stand-up guy (not to mention being sexy as hell) and I need to hire him again soon. Take his advice: he knows what he is talking about and is being very, very honest.

[Jax92]

I would not recommend using a numbing agent. As has been discussed before in the forums, pain is a message your body is telling you that something is wrong. Anal sex should not be painful and a numbing agent may cause you to miss important signals that could lead to injury.

 

When I discuss anal play (and I do it a lot as a sex toy reviewer), I always tell people it's important to go slow and to relax. If you're worried about being clean, start with a warm shower. Don't jump right into sex. Get to know the person and start with a massage. When you're ready, start with just stroking around your anus and rimming. When you think you're ready, the other person can start with just a finger to get you used to the sensation of something being inserted and then move to two fingers. The idea is to slowly get you used to increasing sizes. When you're ready to try penetration and if you're comfortable with it, another suggestion would be for you to be on top so that you can control the depth and speed of penetration. Lastly, avoid playing with your penis, at least initially. When the penis is stimulated, your muscles tense up, including your anal sphincter. And the important thing is to get your body to relax. Remember, it should not be painful, at all. If you feel pain or if it's uncomfortable, slow down and keep trying the warm up techniques above. Good luck and I hope you have a wonderful experience.

[mike carey]

What you need is a firm cocked man to take control, force you to submit and show you what pleasure really is.

 

I know where you are coming from Alec, I wish I had that rather than a half-drunk neighbour who figured me out. Your advice for a first time is grea. You can't undo it and have a second run at it. Looking back, I'd have preferred a longer time to soak up the occasion rather than 'wham, bam, thank you Ma'am (or Sir as the case may be)'.

[Decatur Guy]

Hey, let us all know how this goes. This may be too late for your encounter today, but my 2 cents strictly from my experience:

 

Don't expect a completely discomfort-free experience. A big part of this is learning to distinguish short-term, mild discomfort from damaging pain. It's hard when you're new but it's doable.

 

I'll even go so far as to advise embracing very mild pain and moderate discomfort as an exciting aspect of the encounter. My best fucks as a bottom have been when the top has me mostly in a pleasure zone but has just a tinge of pain to keep things edgy. I don't know what to say: It makes me feel more fucked that way. Let me be clear: I'm not advocating pushing through something that is shockingly painful and has you feeling like your rectum is being torn and you're having trouble breathing. Do not soldier through that. If that is going on, put a stop to it. Immediately.

 

One important thing as the bottom to remember: Put yourself in a physical and a mental state to submit to the dick trying to enter you. A lot of the pain comes from resistance. Resist your natural urge to resist the cock.

 

When it first goes in, your rectum's first impulse is going to be to clinch up and keep out the intruder. Try not to give into that. Mentally, you know you want this cock in you. Remind yourself you have invited this man and this cock to enjoy your most private place. Let him and his dick do what he wants.

 

Physically, it helps to take deep, slow breaths. Try your best not to recoil from the guy. Let him enter you. Like I said above, don't clinch up. Do the opposite of what you think you should do. Instead of clinching, push out if it's hurting. This actually smooths the way for the cock. It may hurt more for a few seconds, but pushing out will quickly make the passage better for both of you.

 

For me, I often have a wave of pain when first being entered. With a good top, it doesn't last long. It's usually a "popped open" feeling right at the hole. I sometimes feel a wave of heat and something like an electrical wave generate down my legs and up to my head from my hole. I've learned to actually embrace that feeling and enjoy it. (And it doesn't hurt to have had a couple of cocktails or a bit of pot. I'm not advocating being drunk or stoned during this. But buzzed can take the edge off ...)

 

Ask your top to let you adjust to his dick being in you before he starts to stroke. When I top and the guy is tight and I can tell he's going to have trouble taking a good full fuck, I go in just a third of the way or so and stop. I then tell the bottom to start squeezing and releasing my dick, over and over. Different speeds. And I get demanding about it. It serves two purposes: Mainly, it makes the rectum eventually relax and give in. It gets worn out, but at the bottom's pace. Secondly, it puts the bottom in a mental state of acceptance.

 

If you're like me, you're going to SWEAR you have to take a dump and/or a piss as the top pushes on. You don't. It's just a feeling. Ride with it and it passes. (Just make sure you've taken a piss before the fuck).

 

Also, be careful about jacking yourself off. This is a very heightened time, and literally a few strokes on your dick could make you come before you really wanted.

 

The bottom line for me: I've learned to incorporate some discomfort into the experience. If I feel full, I go with it. If I feel a little sore, I go with it (it heightens my feel-good sensations, t00). If he's in all the way and I squeeze on his cock and it produces a brief pain ripple, I go with it. But if you feel tearing or your whole body seizing up or he's in a just a few inches and you have pain way up in your stomach, ask him to slowly remove himself from you so you can regroup or try something else entirely.

 

Can't wait to hear how this goes.

[RadioRob]

So today is hopefully the big day. There's been some great advice in the thread, but I'll sum it up below.

 

1.) Communicate with your partner (both before the encounter and during the fun).

2.) Don't try to rush things. Enjoy the moment, and take things nice and slow.

3.) HAVE FUN! Don't try to relive a porno or be a superstar. Just be yourself and relax.

[Yankee]

This is Yankee--reporting back to all my coaches. I can't thank you all enough for bringing me over to the other side. I had my two hour appointment earlier today, and I'm still in this amazing, almost intoxicating fog of ecstasy. Thanks guys!!

 

I'm glad I picked this well-reviewed guy, and I'm glad I booked two hours because it was such a wild, exciting, scary and fun two hours that I called my secretary and told her that I was not coming back to the office. I just left my car where it was, started walking in a daze toward my office, and finally got in a cab and headed instead to go my apartment. As I revealed earlier, I'm in my late 40s and I've only had sex with my wife and two prior girlfriends. In my personal life, I'm an uptight ivy league control freak of a lawyer, and I've never had fun in bed because the women I've been with have never enjoyed it or worked hard at it. Hence my fantasies about guys over the last few years. Well, now I get it! As odd as it sounds, I spend my whole life telling everyone else what to do--coworkers, assistants, household staff, my kids (to a lesser extent, my wife)--but for some reason I wanted to be dominated and broken in by a really dominant and verbal guy (who still knew how to be gentle when going into me). It worked. I listened to all your advice about breathing, about pushing out even when it felt like I was going to the bathroom, about lube and the prostate being my friend, and about telling him exactly what I wanted and didn't want. He listened to everything, and I even warned him that I have a team of coaches (YOU) and we can't let'em down! Without going on too long here (cuz I am writing his review), I can say that today I was transformed from an uptight nerd who was uneasy/guilty talking about sex into a complete whore, and now I can't wait to get back in bed with this guy and some others.

 

I've got to go back downtown now to pick up the car I was too mentally fogged over to drive earlier today after my session, but I think I may have just gotten a new swagger in my step. Thanks boys. Hope I can return the favor sometime soon. ~~Yankee

[BabyBoomer]

Congrats Yankee!!

 

~Boomer ~

[rvwnsd]

Good for you! Glad you enjoyed yourself.

[AdamSmith]

Now you know.

 

Welcome.

[+ purplekow]

I've got to go back downtown now to pick up the car I was too mentally fogged over to drive earlier today after my session, but I think I may have just gotten a new swagger in my step. Thanks boys. Hope I can return the favor sometime soon. ~~Yankee

Swagger or sashay? Either way you may be walking a bit differently but definitely walking a bit taller. Good for you to have the courage to try and find what you need. Since you had a good experience, you can give the escort a plug, after all, he plugged you and turnabout is fair play.