I had been trying to achieve orgasm for months. 18 years old and still not able to achieve what all my university friends had been enjoying for years. The closest I had been to achieving it was by putting a towel on the corner of my rather high bed and spreading my legs wide apart and humping the bed. I got so excited every time and although I had not cum I would spend anything up to half an hour nearly every day.
As my mum went out to work for a few hours every morning, during my summer holidays, I had become used to masturbating every day. My mum and dad split years ago. Every year my mum's dad, grandpa, used to visit us doing the summer holiday. In the last three years his friend, who I had always called Unk (he was no relative), came to visit at the same time. This year Unk arrived two days before grandpa.
On the morning in question I heard mum close the front door behind her and I started to set up my morning masturbation, completely forgetting Unk. As always I was naked as I ground my excited pussy against the roughest towel I could find. I closed my eyes and fantasized about the hunk that I fancied at work. I was really getting into it when I sensed that someone was near me. I dismissed it thinking it was the heating system creaking. I settled myself again and rubbed myself even harder against the firm bed.
Unk's view of events:
As Pauline left I thought I would offer to cook her daughter Emily some breakfast. As I approached her bedroom I could hear some movement and was about to call out when I realized that the sound sounded almost sexual in nature. I quietly looked into the room to be greeted by the most beautiful site. Emily was stretched out on the corner of her bed with her legs as wide apart as possible. Her very full bottom that still had plenty of puppy fat was moving up and down, as she appeared to be humping the bed. I knew I should leave just as quietly as I had arrived but was transfixed by this stunning sight. Emily had always been a little girl to me but right now she was a beautiful young woman seeming to be desperate to fuck her bed with total abandon.
She was clearly fantasizing as she was talking to herself about what she wanted a certain someone to do to her. Unfortunately I could not make out much of what she was saying. I stood and watched her for possibly as long as ten minutes. I was sure that given the energy she was putting into it she would orgasm at any moment. Instead her struggle within her fantasy grew more and more frantic. I risked all to get close enough to hear what she was saying.
She was telling her fantasy friend how she was desperate to cum and to please fuck her harder. It was then that her eyes flashed open and she looked me straight in the eye.
Emily recalls:
I was actually starting to believe that at last I might be able to cum. The sense of being watched suddenly became overwhelming and I looked up to see Unk right next to me. I went to move but he put his one hand firmly on my back and pushed me against the bed.
"I am so sorry I had forgotten that you were here it is so embarrassing I should not have been, I should not have been mas......"
"Masturbating is the word you are looking for. It doesn't need to be embarrassing just about everyone masturbates it is the most natural thing in the world."
I felt kind of defeated by this comment. Maybe everyone does masturbate but not everyone is watched as they do so by someone old enough to be their grandfather. I had been caught literally with my knickers down and wasn't sure what to do next. The decision was taken away from me as he took the baby oil off my bedside table and poured what seemed like half the bottle onto my bottom. It ran down between my legs and covered the whole area. Without hesitation he began to gently massage it into my cheeks.
"There now go back to doing what you have been doing the last ten minutes. It looked like who ever you were dreaming about was just about to make you cum."
I did exactly what he told me to do without hesitation. It was the most wonderful sensation having him caressing my bottom. I found I was not only grinding against the bed with great urgency but I was also pushing up trying to get his fingers to touch me between the legs. I was very quickly as aroused as I had ever been but knew I needed something more for me to stand any chance of experiencing my first orgasm.
Unk picks up the story:
I am not sure why I did what I did in massaging her bottom. It just seemed to be what she needed. Her bottom had the firmness of fitness with softness of her puppy fat. She reacted beautifully to my caress not only returning to her urgent humping and grinding but also pushing back to offer me access to her anus and even possibly her pussy.
As her hip gyrations became more pronounced my fingers started to get dangerously close to the large area of dark crinkled skin of her anus. She had started to fantasize again and was now pleading to be fucked. I did not take it that she was asking me to fuck her but was rather shocked when she managed to get my one finger to just slightly open her beautiful anus. She made it clear that whether in her fantasy or in the reality she was enjoying what was happening and was not impressed when I moved my fingers just out of the reach of her anus.
