Overcoming My Shyness

It was no more than two weeks after my eighteenth birthday that my mother asked me to give Aunt Jean a hand in moving house. She was not my real Aunt but a close family friend and I'd been told to call her Aunt Jean ever since I can remember. Jean's husband had left for the new house already as much work was needed to be done before they could move in. He was to stay away whilst arranging the work and then hire a van on the Saturday to collect their furniture and possessions. I was to help box everything on the Friday and move all the smaller items into the garage for easy loading on the Saturday. It was all straightforward but there was a problem and it was my problem. Four years ago Aunt Jean had caught me staring at her or rather at her chest and I'd been given a good telling off with threats of informing my mother. With that embarrassment and my overwhelming shyness I'd tried to avoid Aunt Jean since then for fear of being told off again or worse.

Come the Friday I set about my tasks with vigour hoping to finish by the afternoon and go back home but Jean had other ideas. When I had more or less finished in the garage she asked me to help in the kitchen and lounge wrapping ornaments and doing all the boxing. It seemed to me that Jean had done nothing although she explained that the big pile of papers was taking longer to sort than she had foreseen. In the early evening I had finished in the kitchen and went through to the lounge and stopped dead in my tracks.

"Come in John, I hope you're able to join me now. Have you finished in the kitchen and can sort these last few ornaments out with me?" asked Jean.

"Yes", I stuttered feeling my face turning crimson. Jean had changed her clothes since I'd last seen her and was now wearing a very short black skirt and the very top that hugged her breasts when she had shouted at me all that time ago.

"Oh good", she said with a lovely smile that was intent on putting me at ease. "Just a few more items to box up and then we can relax and have a drink or two."

I continued working but not now as quickly and mightily tried not to gaze over at Jean. Occasionally she spoke and I had to look but averted my eyes as soon as I could. Nevertheless my eyes took in the protruding breasts and her long bare legs. In her crossed legged position on the sofa I guessed that I should have been able to see her panties had I dared look long enough.

"All finished," she announced as if to the world and not just me in the room. "Finish off that last box whilst I get the wine," she added and left the room.

My eyes followed every movement of her bottom and at last I was able to adjust my erection to an upright position and not sticking out so much. I had kept my groin out of view for what seemed like ages, by keeping the large box I was filling between myself and Jean. It was such a relief that I stroked the front of my trousers in comfort.

"That's much better," said Jean re-entering the room with a wicked smile playing across her lips.

"What?" I spluttered shyly hoping that she had not seen.

"It's time now to relax and enjoy a nice bottle of Malcolm's homemade elderberry wine. Must be careful though because my husband's wine can make me tipsy as well as...........no, better not go there," replied Jean. "Come up here and sit on the sofa with me."

I declined Jean's offer of a glass of Malcolm's wine as I'd tasted it previously and would rather drink piss, not that I know how that tastes.

"Tell me about all your girlfriends," said Jean whilst taking a generous swig of wine.

I was sitting rather stiffly with my hands together in my lap and was both slow and reluctant to answer, as simply I'd never had one of any note.

Jean moved closer putting an elbow on the back of the sofa and leaning over to whisper in my ear. Her left breast pressed into my right upper arm caused my cock to twitch. "Come on tell me. I know that you're shy and perhaps I can help."

As she whispered, with her lips almost touching my ear, my whole body tensed with the hairs on the back of my neck standing up.

"I don't really meet any girls having been to an all boys school but I might when I go to college in a couple of months."

"Oh, you will John, probably lots and what will you want to do with them?" Jean asked cheekily.

"What do you mean?" I said in all innocence.

"Are you going to kiss them?" said Jean and then whispered again close to my ear, "Or something more?"

My cock twitched again with the closeness of Jean's lips to my ear and the strain against the inside of my pants was becoming unbearable. I didn't answer.

"I said I'd try to help especially getting over being too shy. Will you do something for me?" Jean continued regardless of any answer.

"Yes, what is it?" I asked.

"Don't laugh or anything. Will you kiss me to show me how you would do it to a girl?"

Though startled, I simply nodded and started to shake slightly as Jean moved to me and placed her arms around my back. Mischievously she pressed both her breasts to my chest and offered her lips. The kiss was closed lips to closed lips for a short time, more of a long peck, before Jean broke off.

"Let me show you how to do it and I think that you'll like it better. Open your mouth just a little to let my tongue work it's way through as we kiss."

I did as bid and was electrified as Jean's tongue pushed into my mouth whilst our wet lips met softly. Jean moved one hand to the back of my neck and keep pressed to keep my mouth on her mouth. For many minutes like this her tongue sought out all the corners of my mouth and smoothly fenced with my tongue.

"How was that?" asked Jean as she relaxed back to her previous position at my side.

"Fantastic," I replied and found that I was panting.

"I wonder if I should?" said Jean looking directly into my eyes.

I had to look away and was feeling very teased if not tormented especially enhanced by the crooked grin along her mouth. She appeared to be deep in thought for a while and then took a deep breath as if to signal that she had made a decision.

"I've thought of a way of making up for shouting at you a few years ago. Do you remember I got angry catching you staring at my breasts?"

I continued staring at the floor and did not respond.

"You'll like what I have in mind I think," she said and moved to my ear again and whispered, "If you'll promise never to tell anyone."

I did not know what to say or do but was aware that my cock might explode any second after she almost kissed my ear again.

"I'll show them to you to make up for shouting. Okay?"

I turned to look at her hardly daring to believe what she had just said. For the first time I could see her smile was genuine and shyly I nodded my head in agreement.

"Close your eyes and I'll tell you when to open them,"

I could hear a rustle of clothing and felt movement at my side. Whilst my eyes were shut Jean lifted her sweater to around her neck and unclipped her bra. She hid the bra under the rolled up sweater up around her neck and pushing her breasts out said "You can open them now."

I sat transfixed. Here was this beautiful woman with a gorgeous figure showing her perfect breasts inches away from me. She must have read my mind and picked up both my hands from my lap and placed one on each breast.

"Can I have a kiss for showing them? One like I've just showed you how."

She helped me adjust my position as she lay back a little on the sofa for our lips to meet and embolden I pushed my tongue through to search for her tongue. My cock was throbbing and screaming to be set free from my jeans. It was now hurting.

"Like this," said Jean breaking off the kiss to show me how to caress her breasts and gently squeeze her nipples. When she was happy that I was doing it right she returned to our kiss. What seemed like seconds was ages before Jean called a halt.

She poured another glass of wine and found that she had almost finished the bottle. I could see she was thinking again and wondered what would happen next. She looked at me and smiled warmly and with my sudden and new found confidence I took hold of her and kissed her very hard. Her mouth opened in eager response immediately and she clung to me as my hands worked their way back to her breasts. The kiss lasted a good five minutes and again Jean broke it off and was looking flustered.

"You still have a lot to learn," she said as we both moved back to our original positions. With access to me ear again she moved closer and I very nearly exploded in my pants. "You know, " she whispered "had you put your hand up my skirt in that last kiss I probably would have let you."

Jean sat back to watch my response.

"Can I kiss you again?" I asked nervously.

Jean broke out laughing and kissed me on the cheek. "You're lovely."

I didn't know what to make of this or what to do next but it didn't matter as Jean made another decision. Standing up and with her back to me she reached high under her skirt with both hands and slid her panties off.

I was dumbstruck

"I'm enjoying showing you what to do so let me lie down and I'll show you just where to touch me and how."

I watched as she reclined on the sofa with her head resting on a cushion propped against the armrest. She had me half sitting and half laying at her side and when comfortable raised her skirt to expose the object that for at least five years had dominated my entire thoughts.

She took my hand and moved it onto her mound and with one of my fingers traced the very wet line down the swollen lips of her vagina. "What do you think.? How does it feel?"

In all astonishment I answered honestly, "It's wet."

Again she laughed and realised that it really was my first time. "It's not always wet as you put it. It's because I'm aroused and when a woman is aroused her juices run to lubricate her so that a man can enter more easily. Here endeth the lesson," she added and burst out laughing at her own words.

Her laughter subsided quickly as she placed my index finger on her clitoris, not that I knew what it was at the time. With small circular movements she had me at first gently and then more firmly pressing and flicking at this wondrous piece of her anatomy. Her breathing was becoming more and more shallow as she controlled the direction and actions of my finger. She began to gasp and arch her body in an attempt to push back at my finger before turning my wrist and firmly pushing my bottom two fingers into herself. Frantically now her hand was making my fingers work as she wanted until she suddenly bucked her bottom off the sofa and cried out. Her hand grasped mine even more tightly to prevent any further movement and I just watched until she subsided and her breathing began to return to normal. As it did she moved my hand away and lowered her skirt. I lay at her side, again not knowing what to do or what would happen next. I knew what I wanted to happen next and tried putting my hand back but that was firmly resisted.

Jean moved and sat upright on the sofa and then gave me a big smile. "I think that's enough for one day, don't you?" she said and added "this will have to wait for another day." After finishing her sentence she placed her hand on my groin and then looked badly shocked. She pulled her hand away and then opened her hand more and placed it back. I felt that she was trying to trace the outline of my cock. "John, is that all you?" she asked and her eyes were questioning.

"Yes."

"I know we've finished but can I have a look?"

"Yes," I said again and moved both my hands to unfasten my belt. That done I undid the top button before Jean interrupted.

"I'll do it from here," she said and gently tugged down the zipper. "Lift up."

I took to mean to lift my bottom from the sofa and did so whilst she slid my jeans and pants down. She seemed mesmerised as she stared at my swollen and have to say by now painful penis.

"John did you know that you were very big here?" She asked and touched the head very softly.

I did not answer but I did gasp.

"And I had no idea that you were circumcised." Jean smiled looking at my face for the first time since my cock had appeared. "I've never been with anyone that's circumcised. And I've never seen one this big."

She now grasped my stem at the bottom and with her another hand towards the top. With both hands she had still not reached the bulbous head.

"God it's like a baby's arm holding a large plum in it's fist," she spurted out in a fit of giggles. "What's wrong?" she added feeling me starting to shake. "Oh god, are you coming?"

I was nodding my head and breathing in pants whilst a fantastic feeling was building inside my balls and the base of my cock. Jean seemed to know what was happening and still with both hands firmly massaged my whole length. I did explode and Jean desperately put her hand in front to stop the spurts going all over the place. It lasted forever before I finally stopping pumping.

Jean removed her hands and went to get some tissues. She remained silent whilst cleaning her hand and arms plus my stomach and groin area.

"It's not gone down," she said and her eyes indicated that it was my penis she was referring.

I smiled weakly," I might have to come again before it slackens." This was said in all honesty as when I'd had a really big orgasm I'd often played again as it remained erect.

Jean smiled. She gazed at my cock and on cue and with no prompting from me it twitched right in front of her. She was a little startled and transferred her gaze to me and I hoped that she had seen the pleading look in my eyes. She looked once more at my cock, stood up and removed her skirt and laid back on the sofa with her arms open to welcome me.

"Be careful John. You know what to do but be gentle. Just push in a little bit to begin with."

I did as asked and it felt wonderful as the head of my cock met some resistance at the entrance but with a gentle push slipped inside to be enveloped in a warmth I could not have imagined.

"A little further," Jean whispered and I pushed just a little more. "Now move back out and push back........Shit not all the way, come back in!"

We laughed about that later.

Probably to avoid a repeat Jean grabbed both cheeks of my ass and urged a forward move." Now go a little further, and back and now all the way in."

I had done what she wanted so that now my cock was buried to the hilt inside this cave of comfort. Her vaginal muscles were moving and gripping when it pleased her to do so. Everything pleased me.

I could not have known how having my cock inside a woman would be so exciting to my whole body, which was now taking on hitherto unknown power.

My thoughts were broken when Jean said four sweet words. "Fuck me now John."

I smoothed my cock back to her entrance and then pressed back all the way. Jean gasped and bucked at this. A few more times and her grip on my ass tightened.

"Harder," she demanded and as I put my strength into pushing, she cried again "Faster."

She bucked all over the place and it was too much for me as I felt my semen hold for a second and then flood out. I could have died there and then. It's one thing to have come using a hand and quite another to spurt out whilst being enclosed in the most delicious of warm flesh. My cock couldn't stop pumping and twitching and then throbbing. I realised that underneath me Jean felt every little movement and had responded to everything. I moved to get away.

"Stay there," came an urgent appeal delivered almost as a shout. "Don't you dare move."

I settled back down with my cock still thrust fully inside her cunt. It would be ten minutes before she had sufficiently relaxed to let go.

Jean rose and as she was leaving the room asked me to get dressed. She returned quickly in a bathrobe.

"Promise that you'll never mention a word of this before you go."

I promised.

We kissed fairly gently considering what had taken place and Jean led me to the door.

"You know I have a cousin over in Yorkshire that would love to meet you," she said with playful eyes. "I'll arrange it before you go to college if you like?"

I got the message from her eyes.

"I'd love to."

"We'll meet again as well but not for a while. I'll phone though about my cousin."

A further kiss and I walked out of that door and that house a far different person than when I entered what seemed a week ago and was in fact just this morning.

I wondered what Jean's cousin was like as I walked home.