So, I've had this fantasy now for some time and I'm considering trying to make it happen somehow.

The fantasy: To have a female friend sit and watch me masturbate to orgasm. Ideally it'd be someone my age or older, who has little or no interest in actually having sex with me, but is either just curious, or wants to help me experience one of my fantasies for real. I have two friends in mind at the moment.

I'd love to hear about anyone doing something similar. How did you go about asking for it, who did you ask, what rejections have you had, etc..

Looking forward to taking some tips from your responses.

Chris

One of my friends (we went out for a while when we were 18ish) became interested in cocks and men generally a bit later. Used to want to watch me piss ( which i thought was a bit weird so I wasn't really into that) but once when we were about 19 I let her wank me into the bathtub so she could see what cum looked like. Was a horny moment for sure. She loved dicks from then on too. A bit too much some would say.

My wife loves the thought of watching me jerk off in front of another woman. A random woman in public is hot as fuck, but not worth the risk sooooo. Every so often I'll hire a prostitute so my wife can watch me jerk off in front of her.

Have done and still do so... we don't do anything else for the fact that... she's a "Close" friend of my wife...

Found a cell phone in my driveway a few years ago. I look through the contacts to see if I can figure out who owns it. No luck. I look in the photos. No help. Then I look in the videos. To my utter shock I find and play a video taken through my office window blinds of me masturbating! It's forty-six minutes long. There are two other ones that are between 21 and 26 minutes long. Can't believe what I'm seeing. Me gooning out and cumming hard. I hung onto it for a couple hours when it rings! I panic a little and think what the hell. It's some guy asking who I am. I tell him I found the phone. Wants to know where I live. I'm like who's phone is it? His daughters.

Been watched many times by partners, friends, acquaintances, and total strangers.

In high school and college a good guy friend watched me jerk off all the time. Now I jerk off on Skype with other guys. Very hot!!

I once wanked off in front of my sister in law, drunkenly I told her I had knocked one out over a picture I had of her. When everyone had gone to bed, she asked if it was true or was I just trying to shock her. I assured her it was true, and she asked if I would like to do it for real, we were in the kitchen her perched on the table showing her lovely long legs and a glimpse of her lacy panties with the shadow of her bush, me jeans on the floor cock in hand. It was so so good she gave a little gasp when I shot my load over her kitchen floor.

I have had a few female friends as masturbation buddies and never had sex with them. We masturbate together and watch each other or lay next to each other and watch porn or just talk and discuss fantasies, experiences, who/what turns us on, etc. Have had a couple of girls who just wanted to watch me jack off. I usually let it be their suggestion to do any of this, but if it is a friend who you are both comfortable enough talking about sex with each other and not afraid to confess things to each other that you have done or that you like, etc. then if you steer the conversation right (and not be too pushy, anxious or obvious) then you can maybe drop subtle hints and lead them into giving them the opening that if they are comfortable enough with you or turned on enough by the thought of it, they will suggest masturbating together or wanting to watch you. Rarely will I be the one to come out and ask or suggest it, but I have a few times with female friends who I knew would not be offended and felt that they were probably open to it and maybe thinking the same thing. It's better once you have masturbated with/for a few girls already and you confide to a new potential masturbation buddy that you have had girls you have not had sex with and only masturbated with or who liked to watch you and it got you turned on, then they get the thoughts in their head and may just tell you they would like to watch you jack off sometime, or they may just say they would like to see "A guy" jack off. Sometimes the will tell you they love to watch guys masturbate which gives you the opening to tell them you love to be watched or you have wanted to be watched. Some good rules to follow, don't be pushy, be respectful. It may not happen after the first conversation, but don't give up unless they express they are not interested, of course, but at the same time don't make every time you talk to them an attempt to steer the conversation toward sex or about having them watching you. If they are your friend and you want them to remain your friend, you don't want them to feel that is the only reason you are friends with them as this may cause them to start avoiding you altogether. When you do try to talk with them about it, just take it slow and ease into it and be sensitive enough to know if they are feeling uncomfortable with the conversation and ask them if they would rather change the subject. If they do want to change the subject then they likely are not comfortable talking about something like that with you or at least not interested in doing that with you, but if they stay on the subject then they are probably thinking along the same lines as you. Maybe not always, but usually. One good thing to talk about is porn. Ask if they watch it, if they like it and if they do, then ask them what kind do they like best. Then you can ask them things like if they ever masturbate to the porn they like, do they like toys, have they ever let someone watch them masturbate or have they ever watched someone else masturbate and if it turned them on, etc. It definitely helps if they mention that they like to watch people masturbating in porn. then you can tell them that you have had the fantasy of being watched or have had experiences that you have enjoyed having someone else watching you.
You just have to not rush the conversation into a sexual one and keep a constant gauge of their comfort level of the conversation. You don't want them to be uncomfortable or embarrassed and you don't want to come of as creepy. If they are not comfortable talking about it,or even other things you start off talking about or leading up to it, then they won't be comfortable with you asking them to do it. Again, don't lose a friend over it.
Good luck!

Don't waste your money. A couple postings on Craigslist will get you plenty to watch for free. I have jerked off on cam for a female friend while she was at work and had about six of the girls at work watching with her. They loved it so much we set up a time at my place and I jerked off for my friend and three others in person. It was VERY HOT!!!!

then what happens....you have to tell

I gave my address. Twenty minutes later a truck pulls in the driveway. A young woman I recognize from the neighborhood gets out of the passenger side and comes up on my deck. Stunning. Tall, auburn hair, nice rack. She thanks me as I hand it over and starts to turn. I tell her I know what shes been up to and that she should be more careful in the future. Frozen for a couple seconds, she turned and bolted back to the truck and off they went. Thought that was the end of it but I began finding notes in my mailbox telling me how awesome or hot I was. Wildflowers left on my front porch. Lipstick kisses on the porch windows. All this over the course of several months. I started leaving the office porch door cracked open a few inches while I masturbated at my computer again so I could listen better and sure enough. Sometimes a giggle. Once an "Oh yes" whisper. Females voices, hushed. I would try and drag it out as long as I could and always came in huge orgasms just knowing. The notes and "gifts" stopped. I came home one day and the whole front of my property had been TP'd. Nothing more ever since.

As a teen my sister brought her girlfriends over and I jerked off for them. Loved havin girls stareing at my cock and start to touch themselves

I'd love to watch you!