Finger Fucked to First Full Orgasm

I had to attend a business conference and decided I would take my Personal Assistant, Fiona, with me. I thought she would enjoy a stay in a posh hotel for two or three nights, especially as she was leaving me soon to get married in another part of the country. It would be a small 'thank you' for all of her help.

Oh by the way, in case you don't know me, I'm a 41 year old married business woman.

Fiona is a lovely girl of 24 and has worked for me for three years. I knew I would miss her very much when she moved away.

Though extremely efficient she was a strange girl in some ways. She had wonderful features, a really beautiful face, but she dressed in a very modest way, almost old fashioned in her style. It was difficult to say if she had a good figure because of her shapeless dresses, but I suspected that she had a good, firm body. She was also very serious in her manner.

We set off on a Thursday and reached our destination just after seven o'clock in the evening. When we got to reception there had been a mix up with our booking . They had reserved one room with two beds for us, instead of two rooms. As there was no other accommodation available I asked Fiona if she would mind sharing. She replied, with a big smile, that she would be very happy to do this. Her eagerness surprised me somewhat. It was so out of character.

Our room was large with a beautiful view over the countryside and we settled in quite easily and chatted away, mostly about business.

I decided to have a shower, before we went to eat in the hotel restaurant. When I came back into the main area of the room I was wearing only a bath towel. I wanted a change of clothes for the evening. I could see Fiona watching me as I dropped my towel to pull on my thong. I felt sure she was looking at my breasts. I told myself it must be my imagination. I mean, why would she want to look at my body?

Fiona also got changed and I couldn't help but notice how old fashioned her underwear was: big knickers and a heavy duty bra that looked as if it held some healthy sized boobs in place.

We made our way to the restaurant and ordered our food and a bottle of wine. Fiona said that she didn't normally drink wine or alcohol but fancied a glass tonight at a treat.

She actually drank half the bottle and became quite talkative, which was unusual for her. The wine must have relaxed her. She continually glanced at my tits as we chatted. I hadn't bothered with a bra and my nipples were protruding through the thin material of my blouse.

I asked about her forthcoming wedding but she seemed reticent to talk about her future husband or her big day.

We finished our meal and made our way back to our room for a good nights sleep. I had to be up early the next morning.

As I originally believed I was going to have my own room I hadn't bothered to pack any nightwear. I had planned to go to bed naked and masturbate before sleeping. I often do this when away by myself. It helps me to get rid of any stress and, besides, I enjoy it!

"Oh blow it," I thought, "I'll still sleep in the nude." I couldn't see it being a problem so I stripped off my clothes and walked to the bathroom. Fiona's eyes were on me, especially my boobs as they bounced and swung slightly as I walked. This actually made me feel rather sexy.

When I returned and slipped into bed the fresh linen felt stimulating against my skin and the coolness tightened my nipples making them quite firm.

Fiona, much to my astonishment, also stripped off completely and stood still by her bed as if she wanted me to look at her. She had an amazing body. Her skin was pure white, without any blemishes, but her nipples were a dark brown protruding from full, heavy breasts. Her pubic hair was jet black, again a complete contrast to the paleness of her skin.

"Her fiancé is some lucky guy," I told myself.

I was disappointed when she finally pulled on a nightdress. It was a shame to cover such beauty. Before she got into her bed she asked me it would be alright for her to have another drink from the mini bar.

"Of course you can," I answered, "Have anything you want and get me a red wine as well."

Fiona brought the wine to me and as I reached for the glass my bed covers dropped so that my breasts were fully exposed. This made my nipples tingle as she looked at me.

"This is becoming silly," I said to myself, "I'm getting turned on by my young assistant. I must keep control"

I took a sip of the wine while Fiona made her way to her own bed. She lay on top of the covers and almost gulped down her drink.

Though we had been quiet she suddenly looked at me and said, "I'm not sure if I should get married."

"Why?" I asked.

I saw her face redden slightly and she answered, "It's James, my husband to be, he never ... I mean we never have sex. He's never even touched me intimately and he doesn't like me to dress sexily. He says it's wrong before marriage."

"Well some religious people do feel that way."

"I know," she went on, "But he never gets a ... an erection, when we do embrace or kiss. I don't think he fancies me sexually. I get so frustrated at times."

"You must masturbate a lot then," I tried to joke.

"No," she answered, "He says that's wrong as well. I've never had an orgasm in my life. I did have a boyfriend before James and we had sex, but I still never orgasmed. Perhaps there's something wrong with me."

I was quite surprised by her frank talk. It was so unlike her, the alcohol must have loosened her tongue. I then realised that my hand had been involuntarily rubbing my pussy lightly under my bed covers and that I was moist. I pulled my hand away. What on earth was I doing?

Fiona looked at me and burst into tears. She appeared so sad and vulnerable that I got out of my bed to give her a hug. With my arms around her she sobbed quietly on my shoulder as I tried to comfort her. I was naked as I did so.

She took a deep breath and looked at me and said, "I'm going to miss you so much."

Her soft hands started to stroke my back and arms and my skin quivered with pleasure.

She spoke again, "Will you teach me ... teach me to orgasm. Please, oh please."

My own emotions and feelings were all mixed up. Sitting naked and holding such a beautiful girl had my heart pounding, my nipples were on fire and I could sense the strong sexual chemistry between us.

"The best way is to get to know your own body. Masturbate and find out what you like and ..."

"Will you do it for me." She interrupted, "Make me orgasm ... now. Please."

She sat upright and reached for the bottom of her nightdress and pulled it over her head. Her skin was so silky and pure and her large breasts were full of sexual desire. As I watched she opened her legs slightly to enable me to see her pussy lips below the dark pubic hair.

"Touch me," she almost pleaded as she took my hand and placed it on her tummy, "Make me cum."

Her stomach was warm to my hand and, though I knew I shouldn't, I traced a trail down to her pussy.

Fiona groaned as my fingers threaded their way through her pussy hair towards her secret depths. I touched her cunt lips and they yielded to my gentle pressure and opened up to the moistness beneath.

"Don't stop, don't stop," she cried out.

One finger slipped into her and the inside of her cunt felt like liquid velvet. I moved slowly in and out trying to give her the pleasure she wanted and needed.

I moved our position on the bed so that her legs could spread wider apart and I sat between them watching as my lubricated finger pushed its way deep into her as far as I could go.

As I withdrew my finger I pulled all of the way out to feel her clit. As expected it was hard.

"Don't stop, please don't stop," she pleaded again.

I placed fingers at the top of her pussy lips and pulled them apart and then pushed back the hood of her clit. Spreading my fingers further her pinkish-red pearl was now on display.

I lowered my head to flick her hardness with my tongue.

She screamed out, "Oh my God, oh my God."

I inserted two fingers fully into her cunt so I could rub the front walls of her vagina. As I did so I began to suck lightly on her clit. She was so hot and was groaning and moaning with pleasure. Her hands were rubbing her tummy and then up to her tits, squeezing them and pulling on her dark brown nipples. Her pelvis was pushing up to meet my mouth as I continued sucking. She was now beyond control, as I sucked slightly harder pulling her clit between my teeth.

Suddenly she screamed out again, "Oh God, what's happening. Help me, help me."

Her finger nails were digging into her tits, her cunt tightened on my fingers and then she let out a wailing noise as she climaxed for the first time ever. Her body shuddered and as I lifted my head I could see her tits bouncing and her stomach rippling with pleasure.

My two fingers remained inside her and I continued to rub and encircle the front wall of her vagina.

"Hold me, hold me", she said.

I shuffled up the bed and lay next to her, our tits rubbing together and her hands went round me to squeeze me tightly to her. My fingers were still deep in her cunt and she put one leg over mine so that I could continue fingering her.

She was so sensitive I felt sure she would come again as I continued playing inside her honey pot. She whimpered, a strange sound left her lips and I felt her nectar pouring onto my hand as she came once more.

"I love you, I love you," she whispered.

Her lips moved to my breasts and she sucked on my nipples in turn.

"I love you," she said again.

She snuggled into my chest and fell asleep.

I returned to my own bed and masturbated furiously, finger fucking myself to a massive orgasm.

The next morning I awoke early and Fiona remained fast asleep as I left for my conference.

I finished with my business of the day earlier than expected and made my way back to the hotel room. I opened the door and there was Fiona in front of a mirror, stroking her breasts and wearing only one of my thongs. Her own underwear had been discarded.

"Oh," she said, "I'm sorry about the thong."

"That's okay. What have you been doing this today?"

Her face flushed, "I've been having orgasms! Lots of them. It's easy now. Oh, it feels so good."

I just laughed.

Fiona looked a different woman. She was at ease and it was like a heavy burden had been removed from her shoulders.

"I've decided what to do," she continued, "I'm going to tell James that he has to fuck me straight away, as soon as I see him. Otherwise the wedding and our relationship are off. Finished. If he doesn't want to have sex then I'll use the money I have saved and will go travelling the world instead of getting married."

"Good for you. Tell you what lets go to the local town and get you some new clothes - and your own thongs! It'll be my present for your new life, whatever path it takes."

She came over to me and hugged me and then with a big smile on her face asked, "Have I time for another orgasm first?"

"Okay. I'll go and have a shower while you do what you have to."

I returned from the bathroom without bothering to dress and as I did so there was a knock on our bedroom door.

Fiona said, "Oh, that's for me," but before she opened the door she took off her thong so she too was completely naked.

I looked on in amazement as into the room walked a hotel room service guy with a bottle of Champagne in a bucket of ice and two glasses. He only looked to be about 19 or 20 and when he saw Fiona and then me both completely nude he didn't know how to react.

I sat down in a chair pulling a sweater over me but Fiona just stood there and took control.

"Please put the Champagne on the table and would you open it for us, oh, and pour us two glasses."

She stood there letting the young man take in the view of her breasts and everything else besides. She leant back against a nearby dressing table and half sat on it with her legs partly open. Her dark nipples were firm and I could see she was stimulated by the situation as her face was quite pink and flushed.

With trembling hands the guy managed to open the bottle with a loud 'pop' and the Champagne bubbled out. It was very symbolically erotic.

"Thank you so much," Fiona said, with a big grin on her face, and the flustered young man shuffled to the door having one last lingering look at Fiona. I swear she spread her legs slightly wider so that he could see her puffy pussy lips.

When he had left she burst into laughter.

"You naughty tease," I said as I too started to laugh.

"God, that was fun," she chuckled, "Oh the Champagne is from me to say thanks for everything ... my first orgasm and for being the best boss in the world. I'm going to miss you so much when I leave."

We drank a toast to each other and then had another glass of bubbly.

"I feel so randy," she continued, "I've got to get some proper cock soon or I'll burst. I've forgotten what it's like to have someone or something deep inside me. Don't suppose you've got a dildo by any chance?"

"No, but I've got a couple of vibrators, if you want to use them."

Her eyes opened wide with surprise, "Really?"

"In the front pocket of my case if you want to have a look at them."

She went over to my case and I glimpsed her pussy as she bent over to take them out.

"Oh my God," she exclaimed this one is enormous, "Surely you can't get that up your thingy."

"The small one is the size of an average guy and the big one is for when I'm feeling a bit ... nasty ... when I want something special," I explained.

"Fuck! Can I try one, the smaller one?"

"Sure," I answered.

"I want you to watch though."

"Okay."

She went over to the bed and lay down, her thighs spread wide and she put the vibrator between her legs and rubbed it gently over her labia.

"Switch it on at the top," I told her.

The familiar buzz started and she groaned as the vibration stimulated the outside of her pussy.

"Oh fuck, I'm scared", she moaned, "It's been so long ... oh fuck."

Fiona altered the position of the vibrator so that it could be pushed into her waiting pussy. With eyes shut she applied pressure so that the tip parted her cunt. She shuddered, her tits shaking, and she continued so that the hard tool went further inside her and, with a final push, the full six inches were within her secret walls.

There were tears trickling down her face as she began to fuck herself moving the vibrator in and out of her cunt.

She was mumbling to herself, "God, fuck, fuck, fuck ... fuck my cunt ... ohhhh ..."

As one hand was moving like a piston her other was rubbing her tummy as she continued with her self pleasure. Her tits looked swollen, her nipples erect and proud.

"I'm cumming, I'm cumming ..."

My own hand was rubbing my, by now, very wet pussy. I watched her stomach tighten as she lifted her bottom high off the bed. The vibrator was deep inside her, its full length barely visable as her cunt clamped onto it and, with her pelvis elevated, her orgasm erupted.

Fiona cursed and swore, all her decorum had vanished as wave after wave of powerful spasms shook her body. A final contraction of her cunt expelled the vibrator from her body and her fingers pushed at her wetness as juices spilled from her body.

I too orgasmed at the sight of her pleasure and sheer undiluted wantonness, my fingers damp and musky from my own sexual fluids.

Little by little Fiona calmed down and finally lay on the bed weeping.

"Fuck, that was wonderful," she said.

I went and lay next to her and we cuddled each other our breasts compressed together, our tummies touching.

After a period of time, I'm not sure how long, Fiona looked into my eyes and with a big smile said, "Your turn!"

"My turn to what?"

"I want to see you take that big vibrator, right inside you."

I was ready for more sex and though I'd have preferred to be fucked by a long, hard cock I reached for the giant vibrator. I knew I was sufficiently lubricated to take it's full girth.

I opened my legs wide and Fiona moved down the bed so she was looking directly at my cunt.

"Push it in, push it in," she said excitedly.

I put the bulbous head between my pussy lips, relaxed and pushed hard. Four or five inches went into me and I grimaced with pleasure, and slight pain, as my vagina struggled to accommodate the size.

"That is so obscene," Fiona almost shouted out, "Your cunt is so stretched. Fucking hell! Push it in further."

I did as asked and the head seemed to almost enter my womb. I felt so full and complete, it was heavenly. I reached to turn on the vibrations, but only on slow mode at first. I held the vibrator still in the same position and just enjoyed the battery driven motions. I knew I wouldn't take long to cum and I turned the switch to a faster setting.

Still not moving my rubber lover I allowed the vibrations to take over my body and mind as I quivered to orgasm.

"Fucking awesome," said my onlooker as I pulled the vibrator out of me, "Your cunt is gaping open."

Her hand touched me and I jolted with extreme sensitivity. It was if I'd been struck with lightening. Her fingers pulled on my cunt lips until she could fully see my clitoris.

"Your clit is enormous. It's three or four times the size of mine."

I groaned as she latched her mouth onto my hardness and began to suck gently, almost like a baby at the breast. I came again flooding her face. She looked up at me from between my legs, her face glistening with moisture, and said, "We'll leave the shopping until tomorrow. I need to try out your big friend for myself, that'll be another first."

Her lips moved again to my clit and I tried to say, "No more, please, no more," but I couldn't resist.

So the shopping had to wait until the next day.

Can you imagine what this 'new', sexy, uninhibited Fiona was like when we went to buy her lingerie? But that's another story!