Jenny and Jack Pt. 01

The shyness returned again as I felt his hot breath close to my labia. Suddenly I realised with certainty what he was about to do. I had never even dreamed that a man would want to do such a thing.

The only person who had ever seen between my legs was the midwife when I gave birth and my mother when I was a little girl. As I felt his hands encouraging me to lift my legs and open them further I knew I must quickly overcome my shyness to experience something new.

I relaxed my legs and let him push my knees up and apart. I looked down and felt very self conscious and shy as I watched Jack gazing between my open thighs. He briefly looked up and gazed into my eyes saying, "Oh Jenny, you are beautiful down here. Now lay back and relax."

His gaze moved back and I tried to relax. I felt the tips of his fingers gently exploring the moist outer lips of my vagina. Just feeling his gentle touch sent shivers through my entire body.

I felt his hot breath, closer this time and then sighed out loud as he engulfed my moist genitalia with his mouth. I had never felt anything quite like it as I felt his tongue start to probe my wet entrance. It felt almost unbearable as he ran his tongue between my wet lips from bottom to top. I gasped aloud as his tongue briefly flicked over my clitoris.

It was the lightest of touches but felt so exquisite. I realised that after a few minutes any self consciousness I had been feeling was now gone. This wonderful man was driving me crazy with his tongue and I could not resist moving my hips against his mouth in an uninhibited way. As he licked and teased me he moved his hands back up to my breasts. I was already moaning loudly and in ecstasy as I rocked my hips to and fro with Jack's mouth clamped over my genitalia and his tongue teasing my swollen lips. He seemed to know exactly what to do and when. As my own urgency increased I felt his tongue brushing my clitoris more and more. His hands were busy squeezing my breasts and as my orgasm started to rapidly approach he squeezed them harder and harder, almost painfully but not quite.

By now his tongue was permanently pressed against my pleasure bud as I moved my hips faster and faster against his mouth. My screams were rapidly becoming louder and louder as my whole body started to convulse with pleasure. His fingers gripped my breasts tightly, digging into the soft flesh as, despite my movement he managed to keep his tongue pressed tightly against my clitoris. Finally I was completely out of control. I was faintly aware of my screams echoing around the room as my whole body seemed to be filled with the most exquisite pleasure.

Gradually Jack released his grip of my breasts and softened his mouth against me as he sensed my orgasm subsiding.

Finally I just lay there gently panting. I opened my eyes and glanced down at Jack. He lifted his head and gave me a huge warm smile. I could see that all around his mouth was a glistening mixture of my juices and his saliva.

"I assume that you enjoyed that Jenny," he said with a big grin.

I cast my eyes down, feeling embarrassed by how bold I had just been as I said, "Oh Jack that was fantastic, thank you.

We had only been lovers for two days but I felt amazed at how relaxed I was already feeling with Jack. He was still between my open legs and gently playing and pulling the lips of my vagina as he gazed at it. My shyness, for the moment, had gone and I was surprised to find that I was enjoying being so bold and open with him.

Finally he crawled back up my body until his lips met mine. We kissed passionately and I could taste my self on his lips, reminding me of how intimate we had just been.

I could feel his erect penis pressed against me and felt selfish having just had all of the pleasure.

"How can I help with that stiffness I can feel pressed against me?" I asked, already starting to wonder if he would want me to give him pleasure with my mouth.

A memory briefly flashed in my mind of my husband trying to persuade me to let him put his penis in my mouth. It was on our honeymoon. I remembered trying but for some reason finding it amusing, starting to laugh and my husband getting annoyed.

The memory disappeared as Jack said, "I would love you to kiss my penis. Have you ever done that for your husband?"

I chuckled as I told him of the experience during my honeymoon.

"Jack looked thoughtful for a moment and then said, it sounds as though this should be your next lesson then!"

Jack lay beside me on his back looking relaxed with his big erect penis lying proudly on his belly.

"Just start by kissing it Jenny. Move down so your head is in my lap and then kiss my penis.

I felt a little awkward as I repositioned my self and lowered my head down to his erection. I placed my fingers around the shaft, lifted it from his belly and tentatively kissed the tip.

I kissed it a few times and then, with my confidence growing, I started to plant kisses all the way down his shaft.

"Kiss my balls Jenny, kiss and lick them."

As he spoke Jack opened his thighs a little more. I moved my head down and started to lick his scrotum. The skin felt different than that of his shaft but just the realisation of what I was doing made the situation feel very erotic.

I kissed and licked his balls for a while and then moved back to his shaft. This time I licked him, spreading my saliva over him as I gradually made my way back up the length of his shaft to the head.

"Grip my cock in your hand now Jenny."

I glanced up and gazed into his eyes as I did as he asked.

Now move your hand down, while still gripping it and pull the foreskin back from the head of my cock.

I followed his instruction and felt delighted to reveal the head. I had never really seen a penis in close detail before and felt amazed to see the shiny purple head that was revealed as I pulled his foreskin down.

"When you feel ready put the head between your lips Jenny."

I felt like a young schoolgirl with a new toy as I eagerly did as he asked and lowered my mouth over the head of his penis. It felt very smooth on my lips as I pressed them against him.

"Now run your tongue over the head but keep it in your mouth Jenny."

I kept my lips clamped around him as I ran my tongue over the shiny head. It tasted vaguely salty and I wondered if he would want to ejaculate in my mouth and if it too would taste salty.

"Oh Jenny, that feels very good. When you feel ready try and take some more of it inside your mouth."

I slowly lowered my head taking more of him into my mouth.

"See how much you can take Jenny."

I could feel the width of it stretching my mouth as I released his shaft from my hand. It felt big and I was very unsure as to how much I could take.

I slowly lowered my mouth down over his shaft but then the head hit the back of my throat and I gagged.

I pulled back, feeling disappointed as Jack said, "Its OK Jenny, don't worry, just keep it in your mouth.

As I eagerly sucked he said, "It is possible to overcome the gagging reflex you just had. If you want to, try sticking your tongue out first and then, as the head approaches your throat start to swallow and then keep swallowing.

I was not convinced but wanted to give it a try. I felt determined to please him with my mouth just as he had pleased me.

I concentrated on what he had just told me and then tried again. I pushed my tongue out with his big cock lying on top. I then lowered my mouth down slowly taking more and more into mouth. I took it very slowly as the head approached my throat but then started to swallow. As I repeatedly swallowed I lowered my head further. Suddenly I could feel the head of Jacks penis in my throat. The urge to gag was still there but I could suppress it. My lips were now pressed against Jacks pubic hair and I could feel Jack starting to thrust with a fucking motion as I struggled to suppress the gagging. Maybe I was a natural, I don't know, but the gagging reflex passed and I knew that at that moment my greatest and only desire was to make Jack ejaculate.

By now I was kneeling sideways and Jack had placed a hand on the back of my head pushing it down onto him. I moved some more so that the other hand, that was now delving between my legs had better access.

I could feel and sense his heightened arousal as the tips of his fingers parted my wet lips and then pushed inside my still wet vagina; first one then two as he panted breathlessly, "Jenny, I'm going to cum in your throat. Here it comes Jenny, keep swallowing, aghhhhhhhhhhhh."

It felt as though his penis grew fatter in my mouth. I could feel it start to throb and pulsate in my throat. His two fingers pushed urgently into me whilst his other hand forced my head as far down as it would go. His whole body tensed as I felt and tasted him ejaculating his warm salty fluid into my throat. Almost immediately he released my head and I pulled back until just the head of his penis was gripped between my lips. I swallowed his initial spurt as I felt his penis throbbing and still ejaculating between my lips.

His breathing was still heavy and he was covered with sweat as he opened his eyes and said, "Oh Jenny that was fantastic!"

Our eyes met and I smiled; his cream dribbling from my lips and my eyes watering.

We just gazed into each other's eyes for a while as I idly licked my lips and the last few dribbles from his penis each time they trickled out.

Finally he said, "I'm sorry, I got a bit carried away and was a bit rough with you."

I smiled back before saying, "its OK, I loved the feeling of making you lose control."

We both giggled as he slid his fingers from my sloppy vagina with a loud squelching sound. I moved up and lay next to him enjoying the feel of his strong arm as he held me close.

As I lay close to him, his big arm holding me securely to him I felt complete. In just a few days this man had transformed me. I had already done things I would never have dreamed of with him and as I listened to his restful breathing next to me I guessed he had so much more to teach me. After resting for a while I reluctantly got dressed, ready to go home after another late night.

We said goodnight to each other and agreed a time to meet the following morning.

Jenny and Jack

Chapter 4

MY ORGASM IN THE SEXY UNDERWEAR SHOP

The following day we were due to visit another supplier. I had arranged to meet Jack at his hotel without my boss and the supplier was to pick us up there. I arrived at the hotel early and joined Jack for breakfast. As we were drinking our second cup of coffee my mobile rang. It was the supplier. I listened as he explained that an emergency had cropped up and he was very sorry but would like to re-schedule our visit to another time. I told him I would call back to arrange a different day and then hung up.

I turned to Jack and grinned as I said, "That was the supplier cancelling today's visit."

Jack smiled back and said, "provided that your boss is unaware maybe we could have the whole day to our selves."

"Not a problem," I replied, "my boss called me earlier to remind me that he is off on a business trip to China today and that I should look after you for the rest of your stay here!"

We finished our breakfast and headed back to Jack's room. Once inside his room I fell into his arms and we kissed passionately. After a while I pulled away a little and said, "so what has my teacher got in mind for his willing pupil today?"

Jack gave me a huge grin and playfully squeezed my bottom as he replied, "Jenny, do you ever masturbate?"

Despite our intimacy during the past few days his question came as a stark reminder of my remaining inhibitions. I wanted to be completely honest with Jack but felt embarrassed as I replied, "Yes."

"Don't feel embarrassed Jenny, it is quite normal for both men and women to pleasure them selves."

"Really?" I asked. "I somehow thought that I was doing something forbidden or wrong."

"So tell me Jenny, when you masturbate do you have an image or fantasy in your mind?"

My cheeks flushed as I replied, "I usually imagine being with you!"

"What a wonderful coincidence," said Jack, "when I am alone and feeling horny I usually imagine I am having sex with you. I have always had you as my fantasy woman ever since we first met."

"Have you ever watched a porno movie Jenny?"

"A few times," I replied, I found some DVDs belonging to my husband that he thought were hidden away."

"What did you think of them? Did they arouse you and turn you on?"

"Sometimes," I replied, "but I think they appeal to men more than women."

"Maybe," said Jack, "but maybe if we were to watch one together you might enjoy it more."

Jack paused for a moment and then said, "Jenny, I hope this will not shock you but when I fantasize about you and masturbate I often imagine it is you playing the starring female role in a porno movie."

"I see," I said, wondering where this was leading.

Jack hesitated as if trying to make up his mind about his next suggestion.

He held me tight again as he continued, "I have always had a favourite fantasy where I am a porno movie producer and you have come to see me for an audition in one of my movies. So Jenny, today's lesson is a role play lesson. What do you think?"

"I think it sounds like it could be fun but I might need your help and encouragement."

I could sense the excitement in Jack's voice as he said, "first we must find a shop that sells very sexy underwear. I'm sure I have seen a sign post or advertisement to a likely looking shop between here and Downtown."

I knew immediately which shop he was talking about. I remembered seeing it my self and wondering how any woman could have the courage and self confidence to walk into such a place.

"I think I know where it is Jack."

"Good, let's go shopping Jenny!"

It was a nice sunny day and not unbearably hot so we decided to walk. The shop was in a side alley signposted by a cartoon type picture of a semi naked woman. I felt embarrassed as we turned into the alley, hoping that I would not be seen entering the shop. I could explain to anyone who saw me out and about that I was walking with a customer but I could not think of any believable excuse as to why I would be entering a shop selling sexy underwear with him.

It was only mid morning but the shop looked quite dark. I felt nervous as we opened the door and entered. It was not until we entered the shop that I realised why it appeared so dark from the outside. The outer windows were very darkly tinted making it almost impossible to see through to the softly lit interior. As the door closed behind us I looked around at the erotic display inside.

There were life size female mannequins along one wall dressed in various styles of underwear. The predominant colours were black and red and I noticed they were all wearing garter belts and stockings. I had seen stockings in magazines and my husband's porno movies and as I looked around at the array of mannequins I realised how sexy the stockings looked; much more feminine and attractive than pantyhose.

Jack obviously agreed as he placed his arm around me and said, "I would love to see you dressed like that, or," he continued with a mischievous grin, "undressed like that."

A woman of about the same age as me appeared from the back of the shop saying, "can I help you?"

Jack seemed much more confident than I was and I just stood there feeling slightly out of place as he said to the sales lady, "I want to buy some sexy underwear for my wonderful lady here."

"OK," said the sales lady, "I have a selection of styles on the mannequins, if you would like to choose the style then I can show you other colours and variations that I have in stock. Please just feel free to look around. I will be over here when you need me," she said as she walked over to a chair in the corner.

I slowly moved from one dummy to the next and could sense Jack's excitement as we looked at the flimsy lace fabrics barely covering the mannequins. I giggled as Jack stopped in front of one of the mannequins saying, "Jenny, I would love to buy you something like this."

I would never have dreamed of wearing anything so revealing as the set that Jack had chosen.

I looked at the life like dummy, noticing for the first time that it had life like nipples. The bra being displayed was described as a 'quarter cup' and the reason I noticed the dummy's nipples was because the bra did not cover them at all. As far as I could see it was under wired, to give proper support with pretty lace fabric holding and decorating the underside of the breasts leaving the remainder of the breasts from just below the nipple upwards completely uncovered.

Jack made me laugh as he touched the dummy's nipples and said, "Jenny, your breasts would look so sexy wearing a bra like that."

This all felt so new and a different world to the one I had been used to not so long ago. However a lot had happened during this last week and I felt a strong desire to learn more with Jack.

I looked up into his eyes and said, "If you would like to buy me this type of underwear then I would feel proud to wear it for you."

The sales lady must have over heard us and walked across. "It sounds as though you have made a choice for this style," she said.

"Yes," I said, "What colours is it available in?"

"I have this set in Black, red and white, all with matching garter belts."

Jack looked at me saying, "I would love to buy you two sets; one black and one red, what do you think?"

"I was thinking perhaps white but I suppose black and red are sexier, so yes, I would love it if you bought me a black and a red set."

The sales lady then turned to me and said, "Before I check your size and fetch the underwear from the back, are you sure you are happy with this style?

Maybe you should check out the panties first before making your final decision."

To be honest I had not really noticed any detail of the knickers. I had just seen that they looked quite brief and were made from matching lace. As I looked closer I felt my cheeks flush as I noticed another feature of the dummy that I had missed the first time round.

The dummy's had been manufactured to be standing in a provocative pose. Their very accurately detailed breasts were thrust outwards and they were stood with their legs apart and hips pushed forward.

As my eyes moved down to the crotch area of the dummy I noticed that the knickers divided into two as they went between the legs leaving the accurately moulded smooth vaginal lips of the dummy completely uncovered.

I looked up at Jack and all I could say was, "they are very rude!"

He smiled with that wonderful mischievous grin and said, "That is why I chose this set. You are going to look so sexy wearing such daring underwear and I will find you completely irresistible."

As he spoke he reached down and touched the dummy's exposed vagina making us both chuckle.

I turned to the sales lady and pointed to the model saying, "Yes, I would like to have a red and black set of underwear exactly like this one."

I was surprised by how quickly I had felt at ease in the shop. When we first entered I felt very self conscious as though I did not belong. Now I was actually feeling quite excited at the thought of wearing this new sexy underwear for Jack.

The sales lady turned to me and said, "I suspect you know your size but if you don't mind I would like to measure you so that we can be sure of a good fit. If you would like to follow me to the changing room please I will take your measurements."

I followed her to a door at the back of the shop and turned to look back and saw Jack looking at other items that were on display.

He caught the sales lady's eye and said, "We'd like the full VIP treatment please."