Thirty Dirty Questions – Question 25

I am determined to finish this series. It has been over a year!! If you want to catch up on the questions so far my Thirty Dirty Questions page has all the links.

How often do you masturbate and what works best for you?

I was raised a Catholic and sex was not talked about in our house at all. Other than the cautionary “don’t do it”. In addition my mother was very critical of mine, and almost everyone else’s body. She frequently judged people about their weight. It made me very self conscious and private about my own body. I lived quite a long way from town and had very few friends that I could share any thoughts or ideas about sex, bodies, growing up etc. Even when I went to boarding school I struggled to make friends and certainly never talked about sex with anyone. In those days the internet and smart phones were a thing of the future. Learning about sex without a social network or a parent who was willing to talk to you was almost impossible. 

I did overhear conversations between other girls and gained snippets from magazines when I was allowed to buy them and so I did learn to masturbate. I had really very little idea about exactly what I was doing but I did know that I enjoyed it. I remember at one stage I got a bit of a sleep association happening and struggled to fall asleep at night without an orgasm. Not really a good situation when you are sharing a dormitory with six or seven other girls. 

As an adult I didn’t invest in a vibrator or any other sex toy until I was given one by a boyfriend. For some reason I never really took to toys. I just didn’t feel comfortable. Probably because I didn’t really feel comfortable with my body or sexuality in general. This awkward feeling about toys also extended to masturbating. I felt that when I was in a relationship I should be getting sexual gratification from having sex with my partner. Masturbating was admitting that we were getting it wrong. Consequently it was infrequent.

Fast forward to now. I still don’t masturbate frequently. I guess a lifetime of habit and ingrained negativity is still having an impact. I do feel more confident these days but I still find it hard to get alone time to enjoy this activity. Mutual masturbation is not something that is part of my regular couple sex diet. 

So what happens when I am alone? Well I do have a go-to toy. A glass dildo that Mr Jones bought me as a valentines gift a few years ago. There is something about the weight and rigidity that works for me. I still use a finger to stimulate my clitoris and use the toy to penetrate and press against my g-spot. In line with lifelong habit masturbating is usually a means to an end for me. I don’t take time to enjoy or edge. Get the job done, enjoy the warmth and relax for a while. Sometimes even enjoy a short nap. 

Boring I know. 

Send Me a Naughty Picture

Sometimes I get asked by men to send images and videos for them to use as “inspiration” as a rule I resist these requests, especially from men I have never met. Sometimes though, I find it enticing to think about what they do while they are watching me.

The message notification sat on his screen, tantalizing him. Even though he was busy it’s contents still wormed their way into the corner of his mind. In moments of idleness, he found himself remembering her body and the sound of her moans as she was pleasured by her husband and himself. The night had been a last-minute thing. There had been an opportunity and he took the chance. No one was disappointed.

All day he tried to focus on his work, but the memory of her body and the taste of her juice kept stealing into his mind. He caught himself sitting idle more than once with his cock hard in his pants. During his lunch break he stole away and sat in the bathroom watching the clip. He had to mute the sound, but the image was enough. Her legs were spread wide her fingers worked over her little knob, the dildo moved in and out, thrusting just the way his cock had done just a week ago. Had it been that long? It seemed like longer.

Later that night when dinner was finished, and he had showered he lay naked in his bed. Finally, he allowed himself the luxury of watching her. The clip was short, no more than thirty seconds but it was enough to make his cock rock hard in his hand. He began to stroke himself, gripping his shaft firmly moving his hand slowly up and down as he watched the dildo entering her. It made wet sounds lathered with her juice.

In the background the sounds of her moaning accompanied her finger working her clit. His hand shuffled faster as his arousal increased. He could almost taste her juice on his tongue. He remembered her hand on the back of his head pressing his tongue into her. As he worked her clit with his tongue her body writhed underneath him. Orgasms shuddered through her, and he felt her juice filling her mouth.

He played the video again, this time he closed his eyes to listen to the sound of her moans. His hand shuffled faster, gripping him tighter, the way her pussy had when he fucked her. As she neared her climax the intensity of her voice spurred him on. His arousal had been simmering all day barely held back by the demands of work and ordinary life. Now he let it flow through him. His hand shuffled up and down his cock following the familiar patterns of his arousal. He felt the intensity building. He held it back as long as he could, but the pressure became insistent.

One last time he hit repeat and lay back, listening to the soundtrack of her climax. His own climax built in time with hers. Heat and pressure building at the base of his cock. His balls contracted adding to the pressure. His breathing was hot and heavy ending in a small moan. In the background he heard her tone change. Deep guttural moans accompanied by a soft grunt. This time he didn’t hold back. His own orgasm pulsated out of him in hot waves. White liquid squirted out of the end of his cock covering his hand and hitting his chest. His body arched off the bed before the second jet released covering his hand with more of his jizz.

For long moments he lay, panting, his hand relaxed around his cock. A sheen of sweat covered his body before the chill of the air conditioning dried it. After shocks coursed through him and a final small dribble of jizz trickled out. The warmth of his orgasm filled his body from his toes to the top of his head. He took one last look at the final frame of the video. She lay with the dildo resting against her thigh, her hand resting on her sweet mound. If he listened carefully, he knew he would hear her heavy breathing just like his own. For moment it was like they were in the same room.

He may have dozed a little he was not sure. Long moments later he roused himself and moved to the bathroom to clean himself before carefully saving the clip and sliding into his bed. Sleep came quickly, with it came dreams filled with pussy and jizz.

Wicked Wednesday