Who is a person you have masturbated to, but you "shouldn't"

[Leaderoft5b]

So, who have you masturbated to, but you would never admit that you did? Could be someone famous or a real person in your life that you would be embarrassed to admit to?

I've had a couple, but one is a college professor I had for Human Sexuality. I'm a returning student in my mid-50's so there are plenty of inappropriate people. This professor is probably in her late 60's, but has a great body. Petite with a really cute ass. Kinda cute and teaches human sexuality.

Name yours

Mine was a very elderly lady who lived next door to me in the early 2000s. She lived alone and was lonely and used to call me round to help with things she couldn't manage herself such as locking her front door by mistake etc.
One Sunday morning she asked me to help her undo a leaky water pipe behind her washing machine. It only took a few seconds then as usual I sat and had coffee with her. I was only wearing jogging trousers, no boxers and a tee shirt and she flirted a bit by saying that I looked athletic and if only she was 20 years younger etc. She had obviously only just got up before she called me and was still wearing her pyjamas under a dressing gown. For the first time I noticed how huge her tits were even though they were hanging very low with weight and age.
To my surprise I began to get aroused and wished that she would have flirted more to give me the confidence to take things to another level. Unfortunately I got cold feet mainly because I knew most of her family very well who thought I was a godsend for being so helpful to their mum.
Anyway I went back home, dick still semi erect and thought about her while masturbating and wished I'd put my reluctance to one side and stayed with her for the rest of the morning. If only I could have been certain that she was thinking what I had been thinking.

 

[lovethebeach2007]

My adult step daughter.

Maybe she’s doing the same? I play with myself literally every day, thinking about my step dad.

 

[Smoothshavendad]

Mine was a very elderly lady who lived next door to me in the early 2000s. She lived alone and was lonely and used to call me round to help with things she couldn't manage herself such as locking her front door by mistake etc.
One Sunday morning she asked me to help her undo a leaky water pipe behind her washing machine. It only took a few seconds then as usual I sat and had coffee with her. I was only wearing jogging trousers, no boxers and a tee shirt and she flirted a bit by saying that I looked athletic and if only she was 20 years younger etc. She had obviously only just got up before she called me and was still wearing her pyjamas under a dressing gown. For the first time I noticed how huge her tits were even though they were hanging very low with weight and age.
To my surprise I began to get aroused and wished that she would have flirted more to give me the confidence to take things to another level. Unfortunately I got cold feet mainly because I knew most of her family very well who thought I was a godsend for being so helpful to their mum.
Anyway I went back home, dick still semi erect and thought about her while masturbating and wished I'd put my reluctance to one side and stayed with her for the rest of the morning. If only I could have been certain that she was thinking what I had been thinking.

Def got me hard reading this!

 

[12gone]

Everyone i've ever Masturbated too deserved it. And ill let then know.

I just asked my ex for permission and she gave it to me. Now she sends sexy pics to help out.

 

[Jodaily]

I am so not answering this. Seriously pleading the fifth.

 

[MuscularNudity]

Does a birthday party count?

 

[Fenix_Rising]

My husband has a friend that’s 20 years younger than me and damn, he’s even in my dreams. He looks delicious.

 

[drunkwombat]

My husband has a friend that’s 20 years younger than me and damn, he’s even in my dreams. He looks delicious.

We had a number of attractive, (and smart, and funny), women in our office, all under thirty. The joke was that they ruined all other women for us. (The guys in that age bracket laughed, I was dead serious).

 

[JimDee676]

I want to fuck my 25-year-old hairdresser. She's totally hot. I've masturbated to her a few times. I want to suck her boobs, rim her ass and lick her pussy and clit until she cums again, again and again.

 

[Hardguy6]

My adult stepdaughter

 

[TellusMoon]

My now 66 years old MIL (I'm almost 40) this was some years ago.

Also when younger I had a BBW girlfriend and masturbated to her beautiful mother bit I don't think if counts as "I shouldn't" because my girlfriend was the instigator.

I have also masturbated thinking about 2 of my wifes friends that we shared a vacations house together. I don't see that as "I shouldn't". Probably one of their husbands did the same. The other probably not since despite marrying my wife's friend (and high school colleague) he is my wife's uncles (10 years older).

 

[gk6h]

My now 66 years old MIL (I'm almost 40) this was some years ago.

Also when younger I had a BBW girlfriend and masturbated to her beautiful mother bit I don't think if counts as "I shouldn't" because my girlfriend was the instigator.

I have also masturbated thinking about 2 of my wifes friends that we shared a vacations house together. I don't see that as "I shouldn't". Probably one of their husbands did the same. The other probably not since despite marrying my wife's friend (and high school colleague) he is my wife's uncles (10 years older).

Sounds like fun

 

[TellusMoon]

Sounds like fun

Could have been more if werent just masturbatiion

 

[Jodaily]

After thinking about this, I don’t know of any reason not to masturbate to anyone you want to, as we all probably do. You just may want to keep the details to yourself. Or maybe just share with a few close friends. Maybe some really close friends.

 

[PG564E]

"see" myself blowing Peter North multiple times

 

[AndyJacker]

Maybe she’s doing the same? I play with myself literally every day, thinking about my step dad.

Wow that gets a rise out of me.

 

[Duke981]

My wife and her boyfriend

 

[impresso]

I want to fuck my 25-year-old hairdresser. She's totally hot. I've masturbated to her a few times. I want to suck her boobs, rim her ass and lick her pussy and clit until she cums again, again and again.

A similar situation. Because she is always very talkative, tells me a lot about herself, and constantly snuggles up to me in the process... the little devil )

 

[MaxwellSmart86]

Multiple female coworkers, an ex-girlfriend (many times since being married), several of my female friends that I've known since high school (I tend to linger on their beach/pool photos on Facebook), my best bud's wife

 

[asxymann68]

My mother, my sister, school teachers. Multiple Co workers. Waitresses.

 

[Hornysicilian759]

My best friends daughter! Met her at 16(25 now). Not hot but she just does it for me!

 

[Kneeler2u]

Neice, Cousins (Male and Female), Hung guy at the gym, and my daughter and her Girlfriend.

 

[Smoothshavendad]

My beautiful mother.

 

[Snodger]

And I don't do it any more, but Jenny Agutter will doubtless be thrilled to know that I masturbated after seeing her in The Railway Children. Now, I know what you're thinking, but she was 18 in that, albeit playing a 15-year old. And I'm quite sure men all over the planet jerked their mess out to Jenny in that too. Not to mention the rest of her films, because I think The Railway Children was the only one she didn't get her kit off in. They say she did suggest it to the director, but Bernard Cribbins said No, and it detracted from the main plot anyway. But all the same I reckon Bernie did a bit of stonker-stroking himself at the very thought of it all in the railway station toilet. What they call an "off-set shoot" in the film industry.

Hers were the first pubes I saw on TV, in Walkabout. Lovely memories.

 

[tallladiesman]

Hers were the first pubes I saw on TV, in Walkabout. Lovely memories.

She was stunning in walkabout
In my case it was the wife's sister