Taking a guys virginity

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Hey everyone, need your advice

One on my regular massage clients who is extremely shy and timid has asked me to take his virginity. He is older in his late 40's. He is also in the beginning stages of Parkinson. He has told me that he has never once played with his ass nor has he had it played with before by anyone. I have to say I believe him.

Never been in a position like this before. I will be extremely gently and cautious, for obvious reasons. I told him that I would start off with a finger. Just to see if he actually enjoys that first. Progressing further, gauging his pleasurable pain level. Then to me actually fucking him, if he wishes to continue.

Here is the kicker. He wants me to tie him up spread eagle on the bed face down, ass up and gagged. That is his biggest turn on. I always tie him up when he gets his massage. Yeah he is a little freaky shy guy.

If you were asked to do this, what would you do?
 

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He wants it. LOTS of lube man... go slow of course. You know hot to top no doubt. PLEASE under no circumstances even if he asks you to.... do NOT hit him or use any object to hit him (even if that is his fantasy). Not that you would but it could get out of hand so to speak rather easily.

Have fun and keep us posted.
 

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He wants it. LOTS of lube man... go slow of course. You know hot to top no doubt. PLEASE under no circumstances even if he asks you to.... do NOT hit him or use any object to hit him (even if that is his fantasy). Not that you would but it could get out of hand so to speak rather easily.

Have fun and keep us posted.

Oh No.... I'm not going beyond what we have already discussed. I will be very careful with him. Even when I give him his massages, I wrap socks around his wrist and ankles so that the rope will not hurt him. I am very cautious when we are together.
 
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You sound like a really nice guy. Signed consent first! No tickee, no washee. Then tie him down LOOSELY so he can get out. Butt up. If he has to be gagged, 1 sheet of kleenex tissue and some scotch tape across, not in, his mouth. Rim the guy first, then lots of lube, then perform the marital act, very slow penetration. Somehow, I suspect he ain't no virgin though.
 

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He wants me to tie him up spread eagle on the bed face down, ass up and gagged. That is his biggest turn on.
Sounds like a fantasy that works good for masturbation but perhaps not in reality.

He has told me that he has never once played with his ass nor has he had it played with before by anyone.
That sounds similar to me. I was in my 50's when I gave in to curiosity and found a guy to take my ass cherry. Have you ever devirginized a guy? The guy who popped me claimed he had done several virgin guys, and I tend to believe him. He insisted that I would be fucked like a girl (on my back, thighs open and legs up), it would be bareback, and I should expect it to hurt. I got enough information that I could check out his claims and trust him to go bare. Afterwards I figured out that the position allowed him to pin my body under his and prevent my ass from squirming away during the initial painful moments, bareback because the natural insemination is a significant mental part of the first-time experience, as is a little pain.

He prepared me well, including sucking, kissing, fingers, rimming, and worked plenty of lube into me. He respectfully and considerately did what had to be done to my sphincter. It hurt and I cried a little. Being inseminated was a fantastic experience! Overall I was quite satisfied with how he devirginized me.
 

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GIVE him an experience so gentle, loving and pleasurable it is memorable enough that when he seeks it out again after, he looks for that (giving rather than taking). If you can't, for any reason, don't do it.

Bondage with surprise is the best bondage of all, from my perspective. If he experiences sexual violence under control for any amount of time, in the relationship you have, and it imprints, he will seek it again and if you are not available, he will seek it with others. That can be very harmful.
 
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GIVE him an experience so gentle, loving and pleasurable it is memorable enough that when he seeks it out again after, he looks for that (giving rather than taking). If you can't, for any reason, don't do it.

Bondage with surprise is the best bondage of all, from my perspective. If he experiences sexual violence under control for any amount of time, in the relationship you have, and it imprints, he will seek it again and if you are not available, he will seek it with others. That can be very harmful.

We are still discussing what he wants. I will most definitely b gentle with him. We are not in a relationship. He is one of my massage clients.
 

insert_8

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I will most definitely b gentle with him.
It's probably better to err on the side of too gentle, rather than too rough. On the other hand, for bottoms in general there is a fine line between "hurts so good" and "hurts too much" . . . . and for me the effect was amplified when I gave up my cherry. I still remember feeling his weight on top of me, holding me in place, while his massive cock popped and split me for the very first time. (For a virgin hole, either ass or pussy, that first cock is huge regardless of its size.) I said "Ouch!" . . . . then "OUCH!!" . . . . then the muscle ring yielded, a short, sharp pain stabbed through me, and I said "Owwww, it hurts!"

In MY mind, the discomfort was a significant part of the experience of giving up my most personal and intimate hole. The top was controlled, considerate, and patient as he broke me in. He prepared me very well to receive his cock, and worked to reduce my discomfort, but he didn't try to make it entirely painless. He didn't hurt me more than absolutely necessary; and we both knew that Mother Nature would ensure I felt it.

The initial pop hurt about like I expected. What surprised me, and brought out my tears, was the dull pain as he completed the insertion to full depth. It was just starting to feel good when he came, bareback, inside me. THAT was fabulous, even though the sensation was more mental than physical.

I guess I'm trying to warn you about putting too much effort into being too gentle. I expected it to hurt; it did; but the top kept it within my personal limits.
 

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Id say work and stretch him open using small dildo/plugs. Do it over a period of time so he has something to look forward to as he learns about getting his ass owned. I’d never enter him with your cock, just use toys. Let cock penetration be from someone he dates. That way, too, you continue to provide a service and he remains a client.
 
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Id say work and stretch him open using small dildo/plugs. Do it over a period of time so he has something to look forward to as he learns about getting his ass owned. I’d never enter him with your cock, just use toys. Let cock penetration be from someone he dates. That way, too, you continue to provide a service and he remains a client.

Cube ... . I feel pretty sure does not date anyone. His Parkinson and his career I feel keeps him away from that part of his life. He is timid and shy. He has told me that he wants me to "Top him". He will not use "dirty talk"...LOL. We have also talked about the use of dildos /plug, which does not interest him. He told me he wants his first time to be with me. I asked him why? He told me because I was sweet and gentle. That he trust me not to hurt him. Yeah, I think he might have a crush on me, which is fine. It's my thought that he might feel like this will be his chance experience what it feels like before his disease progress further. Still talking, about what he wants and how I will approach this type request.
 

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. . . He told me because I was sweet and gentle. That he trust me not to hurt him . . . .
Has he seen you naked? Erect? Based on your verification photo, if your penis opens a virgin hole it's gonna hurt at least a little - maybe a lot. Don't promise that it won't hurt at all. Let him know it won't hurt more than necessary, and it won't hurt more than he can tolerate. If he is truly OK with that - and your the one who can best judge if he is truly OK with it - then do it.

If he truly expected it to be totally painless I don't think he'd ask to be tied face down. What position do you prefer when you fuck a guy? Or when you get fucked? I'm glad that the guy who popped and split me for the first time insisted on face-to-face, missionary position. My arms, legs, and body had more freedom to respond to being fucked.
 

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Has he seen you naked? Erect? Based on your verification photo, if your penis opens a virgin hole it's gonna hurt at least a little - maybe a lot. Don't promise that it won't hurt at all. Let him know it won't hurt more than necessary, and it won't hurt more than he can tolerate. If he is truly OK with that - and your the one who can best judge if he is truly OK with it - then do it.

If he truly expected it to be totally painless I don't think he'd ask to be tied face down. What position do you prefer when you fuck a guy? Or when you get fucked? I'm glad that the guy who popped and split me for the first time insisted on face-to-face, missionary position. My arms, legs, and body had more freedom to respond to being fucked.

He has never seen me completely naked, just in my underwear. Up until now he has not been interested in any type of " sex " with the exception of my jerking him off... I know he is now opening himself up to newer sensations. He knows it's going to hurt, we have discussed in details about how it will be for him. That's why he trust me, I don't bullshit around a questions. If he asks me something. I give him a direct honest answer. I know the difference between pleasurable pain and real pain. I will gauge his reactions. I seriously doubt , we will get to a full fucking.... We will see, if and when this happens

As for position, I prefer being fucked or fucking doggie style... as for him being tied up, he requested split eagle face down, and gagged. He is my client, It his choice not mine.
 

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I see no problems with fulfilling his request. My question would be are you being paid to do this ? If so, I would seriously decline, but that may be a concept that you are comfortable with. If you haven’t thought about it, ask yourself if you are comfortable selling your body or having sex for money. It can be some emotional baggage for some.
 

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It's probably better to err on the side of too gentle, rather than too rough. On the other hand, for bottoms in general there is a fine line between "hurts so good" and "hurts too much" . . . . and for me the effect was amplified when I gave up my cherry. I still remember feeling his weight on top of me, holding me in place, while his massive cock popped and split me for the very first time. (For a virgin hole, either ass or pussy, that first cock is huge regardless of its size.) I said "Ouch!" . . . . then "OUCH!!" . . . . then the muscle ring yielded, a short, sharp pain stabbed through me, and I said "Owwww, it hurts!"

In MY mind, the discomfort was a significant part of the experience of giving up my most personal and intimate hole. The top was controlled, considerate, and patient as he broke me in. He prepared me very well to receive his cock, and worked to reduce my discomfort, but he didn't try to make it entirely painless. He didn't hurt me more than absolutely necessary; and we both knew that Mother Nature would ensure I felt it.

The initial pop hurt about like I expected. What surprised me, and brought out my tears, was the dull pain as he completed the insertion to full depth. It was just starting to feel good when he came, bareback, inside me. THAT was fabulous, even though the sensation was more mental than physical.

I guess I'm trying to warn you about putting too much effort into being too gentle. I expected it to hurt; it did; but the top kept it within my personal limits.
thanks- that sounds so perfect:
he didn't try to make it entirely painless...
the dull pain as he completed the insertion to full depth...
 
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