What's the best way to take someone's virginity?

[Marlowe]

I have a guy, older, maybe 55 who loves to suck cock who really wants me to take his ass. So much so that he's offering me weed. I want to too. The idea of loading a virgin late bloomer seems awesome. trouble is I remember my first time and I know how much it hurts and how tight I was. Any ideas on how to make him comfortable to go through with it? And if not share your stories: how do you fuck virgins?

[bredbiyou]

Get him to pick a position that allows him to relax his body, while also allowing you access to his hole. This will vary from one guy to the next, but I've always found that laying face down on one's stomach with a pillow propped under the hips to slightly elevate the ass works quite well. Once he's in position, rim him for as long as it takes to get his hole to relax. Apply lots of lube to both your cock and his hole. No condom, obviously. Poppers. Enter slow, but steady. Remind him to breathe.

Hope it goes well for both of you!

[Guest Memphian]

It might not be as difficult as you think to top him.  By the time I finally got fucked I had spent a lot of time practicing with my wife's dildos and knew what to expect and how to relax and take it.  If he's wanted this for a while I bet there is a good chance he's been engaging in ass play.

 

 

[PhoenixGeoff]

22 hours ago, Memphian said:

It might not be as difficult as you think to top him.  By the time I finally got fucked I had spent a lot of time practicing with my wife's dildos and knew what to expect and how to relax and take it.  If he's wanted this for a while I bet there is a good chance he's been engaging in ass play.

This may be true.  I'd talk it over with him first. 

If he hasn't engaged in any ass play before, start out very small and slow and work your way up to getting your dick in him.  Let him get used to his ass being a sexual organ.  Lots of rimming, followed by careful fingering, perhaps a toy or two.  It might take more than one session before he's ready for your cock.  Virgins demand patience.

And absolutely make sure you have a good, long conversation about HIV and other STDs with him.  He can assess the risks himself and make his own decisions of course, but in order to make an informed decision, he needs to be actually informed.  Properly informed.

To be clear:  you should not be influencing him to take you raw in any way whatsoever; just present the facts neutrally and objectively, let him do his own research, and then respect his decisions.

[HardOneLA]

Great question, bud.  For most of my life I was a top, though I would suck cocks.  When I was 50 I was diagnosed with prostate cancer, and underwent proton radiation.  Despite all their assurances and promises there was some loss of function (E.D.) and it took stimulation for me to get a (semi) hard on.  But I no longer really had the confidence to fuck.  At the time I was in a relationship and we were truly in love.  While I'd always been a top, I also had always known that my persona was sub, and that somewhere deep inside I was meant to serve cocks.  One day at our then house in Palm Springs, outdoors by the pool, under the blazing sun, we were fooling around.  Finally he said, "I want to fuck you."  He never had before, we had always had extremely hot oral sex.   I think we may have smoked a little pot, and I love poppers.  So I got on a chaise, and we lubed up.  He can get a hard erection at the blink of an eye so was ready.  Each time he tried to mount me it hurt so much that I'd cry out, until he said, "Well if it's gonna hurt that much forget about it."  Forget about it?  I couldn't.  I knew it was my true calling and I had to fulfill it no matter what.  So with persistence, poppers and lust, we continued until he took my cherry and was able to mount me.  As he got further in and began to fuck me the pain turned to ecstasy, the real pig in me came out and he took me to hog-heaven.  Damn, why had I waited all these years for this?!?  Although I do attribute that to saving me from the AIDs crisis days.  From thereon there was no stopping - over time he fucked me in every room, every locations (indoor, outdoor, public, etc), every position.  I was finally fulfilling my higher calling.  Sadly we have parted, but now I am on PrEP and free to pursue making up for lost time  - which I do!  I have zero regrets about not topping anymore.  However, someone sucking my cock absolutely brings me into full heat and beg to be fucked.

Sorry to be so long winded, but I guess the bottom line is:  Your friend has to have this true inner desire to be fucked and then he will be.  And once he does, like me, he'll wonder why it took him so long.  Oink!

[chargedodger]

3 hours ago, HardOneLA said:

Great question, bud.  For most of my life I was a top, though I would suck cocks.  When I was 50 I was diagnosed with prostate cancer, and underwent proton radiation.  Despite all their assurances and promises there was some loss of function (E.D.) and it took stimulation for me to get a (semi) hard on.  But I no longer really had the confidence to fuck.  At the time I was in a relationship and we were truly in love.  While I'd always been a top, I also had always known that my persona was sub, and that somewhere deep inside I was meant to serve cocks.  One day at our then house in Palm Springs, outdoors by the pool, under the blazing sun, we were fooling around.  Finally he said, "I want to fuck you."  He never had before, we had always had extremely hot oral sex.   I think we may have smoked a little pot, and I love poppers.  So I got on a chaise, and we lubed up.  He can get a hard erection at the blink of an eye so was ready.  Each time he tried to mount me it hurt so much that I'd cry out, until he said, "Well if it's gonna hurt that much forget about it."  Forget about it?  I couldn't.  I knew it was my true calling and I had to fulfill it no matter what.  So with persistence, poppers and lust, we continued until he took my cherry and was able to mount me.  As he got further in and began to fuck me the pain turned to ecstasy, the real pig in me came out and he took me to hog-heaven.  Damn, why had I waited all these years for this?!?  Although I do attribute that to saving me from the AIDs crisis days.  From thereon there was no stopping - over time he fucked me in every room, every locations (indoor, outdoor, public, etc), every position.  I was finally fulfilling my higher calling.  Sadly we have parted, but now I am on PrEP and free to pursue making up for lost time  - which I do!  I have zero regrets about not topping anymore.  However, someone sucking my cock absolutely brings me into full heat and beg to be fucked.

Sorry to be so long winded, but I guess the bottom line is:  Your friend has to have this true inner desire to be fucked and then he will be.  And once he does, like me, he'll wonder why it took him so long.  Oink!

Wow am stunned!Very well written.:)

[chargedodger]

If he is interested in it and wants to learn how to bottom he must have a part of his sexual being that needs to be released.He sounds like a bird with wings he has never used.All that is needed is a good comfortable seduction,the moment a hard cockhead touches his pucker nature will take over.:)