Woman's First Orgasm

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.

"Oh deeper, deeper push it right in. I need to cum so badly. Fuck my pussy I need all of your cock."

If I had been concerned earlier now I knew I had gone to far. Her fantasy world and her reality were beginning to get confused. She was still using the name of some boy she knew but it was my finger she was muddling up with his cock.

Emily again:

I don't know if he was deliberately teasing me with his finger but he seemed to be stopping just when I was praying that I might just get there. What he was doing was unbelievably sensual and I loved every single touch. I needed more.

"Unk I have never had an orgasm and I think I might be able to get there if you help me. Your finger around my bottom feels wonderful but I need a little more please help me I am so desperate. All the girls at work say how wonderful orgasms are I so want to know."

The whole feel of his hands changed immediately. He still caressed the whole area but when his one finger found the centre of my anus he allowed me to push myself up so it slipped in. I thought my heart was going to stop. My breathing did. With his finger still just inside my bottom he pushed me flat against the bed. Now I could hump the bed and still enjoy pushing back onto his lubricated finger. I could rub my pussy and fuck my bottom very easily.

"Please fuck my bottom with your finger I think I might just cum."

He did what I asked and it was lovely. I was now getting demented in my effort to have the illusive orgasm.

"Would you like me to try something different my lovely?"

Unk finishes the job:

When she admitted that she had never had an orgasm my heart really went out to her. When she asked me to fuck her bottom I knew she was desperate. By now she had been working for an orgasm for nearly half an hour.

When I offered to try something different I was certain I could put her out of her agony. I applied more baby oil to the area and removed my finger from her bottom. Her cry of anguish was soon replaced by a satisfied moan as I pushed my thumb into her rectum as far as it would reach. It felt like velvet in there and when I lifted her hips off the bed the fingers on the same hand were able to find her very plump and wet pussy. I decided not to enter it as I thought she might well still be fully intact.

I knew she would not last long now before experiencing her first climax and was in no hurry to rush it. With my other hand I lifted her chest off the bed and found her smallish but perfect boob with my hand. Her nipple that I could not see felt erect if not very big. It was big enough for me to roll it between my thumb and one finger.

The noises she was making were the sexiest I had ever heard. Within seconds of my fingers finding her clit she was humping my hand and wailing as she exploded in an orgasm that was as strong as I had ever seen a female have. I rode with it fucking her bottom and playing her clit in time with her hip thrusts that threatened to displace me.

Emily gets there at last:

I knew the minute this thumb pushed deep into my rectum that nothing would stop me from experiencing my first fabulous orgasm. The fingers on my clit and the squeezing of my nipple were icing on the cake. As long as I live I will never forget that first stunning orgasm.

Unk was with us for over two weeks and every time we managed to engineer time together he would use his fingers to bring me to spectacular orgasms. He refused to go down on me or to let me touch him sexually in any way. I probably had a dozen orgasm and they are still some of the best I have ever had.

It wasn't for years after that fortnight that I learned that Unk and my mum were lovers for many years. She admitted to knowing about my orgasms at his hands. She had engineered my time with him because she said that the best sex with him was always after he had enjoyed time with me first.