Awakening Jessica

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65-years old virgin losses cherry to young man.
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I was raised in a small rural town in Scotland. I had quite a good life, albeit parochial and lonely. It did not help that I was plain and dowdy, certainly not pretty or sought after. As a teenager, I was the wall flower left guarding the handbags, whilst the other girls danced the night away. Time passed by, they found partners and began to form close relationships. I became more and more uncomfortable, like a gooseberry, when invited to come along on nights out with them. I knew they did not really want me around but felt obliged to ask. Eventually, I started making excuses, stopped going out and settled into a solitary life.

In those days, girls left on the shelf had few options. They had to have a good job. Locally, there were very few possibilities and these were as domestics or cleaners. Not my forte at all. I, therefore, moved to the city and took on a junior administration position at a development company. I have been there for forty-five years and worked my way up to Senior Projects Manager. My career was productive and rewarding, but the lack of a soulmate or family of my own left an emptiness. Colleagues often remarked that I was so lucky to be free with no commitments, but it wasn't true. I was old and lonely.

Two years ago, a young man bought the house next door. George was Facilities Manager at a Biotech company. He was thirty-three, single, athletic and handsome. He always seemed to be busy, rushing off to work at all hours. Other than an occasional 'hello' in passing, we did not meet during the first month. Then, one day I was working in my garden when he came back from a run. He looked over the hedge and asked if he could help. I said that I was struggling clear a large patch of weeds and would be glad to have extra hands. Within a short time, the area I had worked on for so long was clear. That broke the ice. We sat and chatted for hours and had a meal together.

George was from the South of England but had been posted up here three years ago to set up a new research facility for the company. Although it was meant to be a short-term position, he had fallen in love with the area and decided to settle down here, traveling south on the occasions that he had to be at company headquarters. He had relationships in his late teens and twenties, but none that lasted. The breakup of the last had been particularly bad. From then, he concentrated on his job and rose rapidly to his present position.

I was amazed that he was telling me all this but glad he felt comfortable enough to do so. I was sad that he had decided to be a singleton. It is not the good deal that is often inferred. Also, he was good-looking, courteous, hard-working and a good companion. He would have been a great catch. I even had the fleeting thought that it was a pity I was not thirty years younger, but I would never have had a chance anyway. From then on, we became good neighbors. He would come around once or twice a week to check that all was okay and see if there were any little jobs needing to be done.

I became more and more at ease with George over the following months. So, when he came in one day to find me in floods of tears, I felt I could tell him what was wrong. Things had been going badly at work for a couple of months, putting me under a lot of stress and making me feel fragile and down. Over a couple of weeks, several members of staff had come in with their new babies. They looked so happy and proud as everyone gathered around and billed and cooed. I felt completely on the outside again and it had just hammered home to me how sad and lonely I had become. Life was flying past and I had nothing to show for it. George was trying to calm me, when I just blurted out "I am not even a proper woman, I have never been with a man, I am a sixty-five-year-old virgin". He was shocked. I had not talked about my private life and he had assumed that like him I had relationship problems earlier in life and decided it was better to be single.

The tears continued to pour, enough to soak George's shirt. In my distress, I had not realized he was holding me close to console me. I pulled away, saying I was sorry.

"That is okay. Dry your tears and compose yourself. I will change my shirt and then we can have a long talk about this."

I was ashamed to have broken down because I prided myself on being in control. That brought on the tears again. George came back, got me some tissues and we started to chat. He did not beat about the bush. Your view that 'you are not a proper woman' is gnawing away all the time and badly affecting you.

I blushed for the first time in many years but admitted that it was an issue. "I have been ignoring it for so long. It is a relief even just to talk about it. There have even been times recently when I have considered using a male escort to lift this albatross off my back, but I don't know how to I could arrange that."

George was so taken aback that he sat there in silence for several minutes, but finally clasped my hands and said, "No, that is not the answer, in fact, it would be very risky and dangerous in many ways for you. Let me think about this. It is late, so you should go get some rest and we can talk again tomorrow." He went off home, I went to bed and slept through to morning.

George had not appeared by midday, so I went looking for him and found him asleep at his computer. I woke him to check that he was okay. He said that he could not sleep last night and had decided to some research on the internet. Exhaustion had finally kicked in and he had fallen asleep in the early morning, but not before he found the information he was looking for and coming up with a plan.

He was very quiet whilst we ate lunch, but then explained that he had been searching for information on sex and the elderly. "If you filter out the fairy stories about the sixty-eighty years-olds going at it like rabbits, you come down to a few well-documented studies that show many couples of that age still regularly make love. Also, there are credible cases of women that did it for the first time in their sixties. A key thing that all emphasize is that the couples must be close, caring and at ease with each other for it to be good. If not, the experience can be very bad and physically and mentally damaging."

I started to cry again. "There is no hope for me then."

At that, George came over to me and kissed me lightly on the lips. My heart missed a beat when he said, "Shush, I have an idea. It will take some time, but if you want I will help you."

My knees almost went to jelly. "Are you proposing to make love to me?"

"Yes, that is the eventual aim, but we have a lot to do before that can happen. We need to become a couple. Join me on the sofa, if you want to start now."

I almost skipped over to it, he took me in his arms and gave me a long lingering kiss. He released me, but I pulled him back and planted a kiss on him. This was so good. We smooched on and off all afternoon and late into the night. He really took my breath away, but he was also a good teacher and I was giving in equal measure by the end of the day. My head was in a spin of new sensations and emotions. I was reluctant to stop in case the moment was lost forever, but I slept so well that night.

Next morning seemed to drag on forever, I was on tenterhooks until George came over at midday. I practically pounced on him and we were soon making out on the couch as before. He started to kiss me on the shoulders and neck. This was good. I felt his hand move up towards my breast, but I tensed up and brushed it away.

"I am really sorry. I did not mean to do that."

Bless him, he said he was not surprised. "For most of your life, you have had little physical contact with anyone. Your mind and body reacted instinctively against my invasion of your space. Imagine what would have happened if I had tried something even more intimate."

I could now see what he meant before. I would have frozen stiff at any attempt at sex. This scared me, but I was even more worried that it would put George off and he would stop. No fears, he pulled me back into an embrace and we returned to snogging. After a while, he started to kiss me again on the neck and shoulders. He told me to take hold of the back of his right hand. "I am going to move my hand up to your breast and start to stroke it. Keep hold of my hand and pull it away if you feel uneasy."

His fingers gently stroked my breast. I felt myself relaxing and warming to the sensation. Indeed, I grabbed his left hand and placed it on my other breast. Even through the clothing, it felt so sensual. He was nibbling at my neck when he said, "release my hand if you are comfortable. I will explore some more. Why don't you do the same?"

I quickly found that I am particularly sensitive between the breasts and around the belly button. I released his other hand and was soon myself feeling his strong muscular body. We spent the rest of the day making out. The only area of me that George had not touched was down there. Surprisingly, I was disappointed, but when I asked he said that he wanted to be sure I felt safe before going near my pussy. Judging by how I had reacted to the first touch of my breast, he was probably correct.

It was getting late, so reluctantly we separated and went off to bed. As George was leaving, he said, "I will be back tomorrow evening. Would you be willing to be in your pajamas that early?"

"Why?"

I quivered when he said, "we have made out fully clothed, but if you are comfortable we can do the same tomorrow with only two thin layers of cloth between us. No underwear or thick outer clothing to mask contact."

It was difficult to concentrate at work next day, but eventually, it was over and I found myself at six o'clock sitting on my sofa in my silk pajamas. George arrived and handed me a package, a pre-prepared meal for us to share. I set the table whilst he went to change. We had our meal and then retired to the sofa, where for a couple of hours we made out as on the day before, except that every response was heightened because there was almost nothing between us.

Later, when I was already hot, George started to gently stroke my thighs. I was already getting interesting sensations by the time he was closing in on my pussy and I spread my legs slightly to allow him better access. As he stroked my pussy through my pajamas, strong pleasurable sensations began to manifest themselves and I became wet down there.

George then stopped and held me close. I could feel his chest beating against mine. He whispered to me, "Do you want to take this to another level?" Although unsure what he had in mind, I had enough confidence in him to say yes.

"Let's sleep together tonight. I assure you it will just be to sleep." With that, he took my hand and led me to the bedroom. He slipped into my bed whilst still holding my hand and invited me to join him. I was apprehensive. I had never shared my bed with anyone but quickly got in there beside him. We had that uncomfortable period where we both stared at the ceiling not sure who should make the first move. George took my hand, pulled me towards him and kissed me. We cuddled together and fell asleep. I woke next morning with my head lying against his chest, feeling it gently rising and falling. I was so happy and at ease and as it turned out, I would never to sleep alone again.

We smooched for a while in the morning, but then realized we had to get up. It was quite a dash to get ready, have breakfast and get to work on time. Again, it was a long day. I could hardly wait to get home. After our evening meal, we settled on the sofa and made out. Later, George took me to the bedroom and we continued petting on the bed. After a while, he stopped, held me close and said, "take hold of my hands as you did the other day. If you are uncomfortable or scared, pull my hands away". With that, George slid his hands under my pajama top, moved them up to my breasts and cupped and gently stroked them.

I gasped but in pleasure.

"Are you ok?"

"Yes, keep going." With that, he uncovered my breasts and started to kiss them and suck on the nipples. Wow!

He whispered, "undo my top and take it off."

This took quite a while since I was distracted by the sensations coming from my breasts. Once his top was off, George took mine completely off as well. I kissed and sucked on his nipples and rubbed his chest, whilst his lips worked vigorously at my breast. He broke off and started kissing down my abdomen right down to my waistband, whilst I ran my fingers up and down his back. He really liked that and I found it good when he was kissing and licking around my belly button. George started to gently stroke my thighs. I was damp and hot and asked George to go to my pussy.

He was hesitant at first but then said: "Okay, hold my hand as we did before". He lifted the waistband and slipped our hands downward. All was well as he gently caressed my mound and moved down towards my vagina. Then, I suddenly froze, pulled my legs together and started to shiver. George pulled his hand back immediately and just held me tightly in his arms.

I burst into tears. "What happened, it was going so well?"

George took me in his arms and pulled me on top of him. We were lying there, belly to belly, breast to breast, with my body moving up and down in rhythm with his chest and my tears dripping on his cheeks.

He looked straight into my eyes and said "Shush, I thought it might be too soon. That is why I was hesitant. Think how far we have come. Could you have imagined a week ago that we would be lying together like this?

We rolled over to be side by side and he kissed me more passionately than ever before. He then started to kiss and stroke my breasts and suck the nipples with great intensity. The effect of all this was making me so aroused, I was in a dream. I did start to feel some additional sensations, but was not sure what they were until George whispered, "check where my hand is."

It was now caressing my clit and pussy lips and wow, it felt so good.

"I was going to wait but recognized your fears might be worse by tomorrow. I deliberately went heavy on you and started to stroke your pussy when you were otherwise preoccupied. Your pussy's high sensitivity took over and my goodness it certainly responded."

I held him tight and kissed him heartily. I was ecstatic. "Thank you. I was so scared when I tensed before that you would never get near me". We kissed again and fell asleep in each other's arms.

I had a very unsettled day. Although last night had worked out okay, in the end, thanks to George, my sudden tensing and freezing unsettled me. It appeared to be out of my control. I was worried that it could happen again at any time. George and I settled down on the sofa that night, but I could not get comfortable. He picked up on this and said, "you are uptight after last night? We need to get you relaxed".

George got up, went to the bathroom and ran a bath. I followed him through, undressed, lowered myself into the warm scented water and had long relaxing soak. George came back with towels, got me out, slowly and gently dried me off and led me through to the bedroom. He told me to lie face down on the bed and proceeded to give me a body massage. He was an artist. I should not have been surprised. I could feel tension being released from my body. He then turned me on to my back and continued to massage me, particularly working on my legs up towards my inner thighs. I was now relaxed and getting aroused.

He started to kiss and lick my inner thighs and then around my clit and pussy lips. The feelings triggered just by his warm regular breaths ruffling through my fuzz were so unexpected and stimulating. He ran his tongue over my lips, between them and into me. He licked and licked and licked. I felt myself becoming so wet. He stopped and started to gently lick and suck on my clit. There were so many sensations that I was in a daze and he had his forefinger between my lips and into my vagina before I realized it was happening. Another diversionary tactic. It was tight, but he gently moved his finger in and out and around my vagina. I admit to pushing myself forward onto his finger to heighten the sensation. He kept going and soon waves of pleasure were flowing through me.

George lifted me up, pulled back the duvet, lay me in the bed, slid in beside me and pulled the covers over. I gave him a long lingering kiss and fell asleep thinking of all that had just happened. It was later during the night that I understood how far we had come. We were sleeping together naked for the first time. I pulled myself close, to get the full sensation of his sexy body next to mine.

I was surprised to find he was not there when I woke up next morning. However, he soon reappeared with breakfast on a tray for me. I blushed when he said, "you look so gorgeous and sexy lying there. I would prefer to be in bed with you, but I must go to a meeting so will just have to contain myself until this evening."

"There is something I want you to do." He handed me a blindfold and a pair of ear plugs. "Try them out. If you are comfortable, I want us to make out tonight whilst you are wearing them."

I looked quizzically at him.

"Touch, sight, and sound are important in intimacy. If you take any of these senses away, the others become more reactive and responsive. Despite everything we have done together, you have only had limited intimate physical contact. I want you to experience it in its purest form. You will come to appreciate its impact on the body and mind and will always be highly responsive to it.

I thought about this off and on over the day. I shivered at the thought of not being able to see or hear what was being done to me but was intrigued to find out what it would be like. It is a mark of how safe and confident that I now felt with George that I decided to give it a go.

We were lightly petting on the bed that evening when George asked if I was willing.

"Yes, I am ready."

I held on to him as he fitted the blindfold and ear plugs. I was quite disorientating at first but he held me close until I settled. He then placed me on the bed and lay down beside me.

"Tell me to stop, if at any time you feel scared."

He held my hand and then I felt his lips on mine. That lack of any forewarning made the kiss even more sensual than usual. He slowly stroked and kissed his way down my body until he was tonguing and fingering my vagina. My body was tingling and highly sensitive to every touch and stroke. Who knew it could be as good as this.

Everything to that point had followed the normal pattern, but then George started to mix things up, switching his attentions between my erogenous zones. He would go from fingering my pussy to sucking my nipples, to kissing my lips, stroking my legs or licking my belly button. It was difficult to keep track of where he was or what he was doing. Sensations were flowing into me from all over. I became very aroused, more so than ever before. At one point, I was sure that George had three fingers in my vagina, but then he was caressing my breasts.

I was in rapture when again I felt three fingers penetrate and push my pussy lips apart. I soon sensed his fingers slowly pull out, but to my surprise, I still felt stretched and full down there. His hands cupped my breasts and he whispered, "take the blindfold off and look down".

Oh, wow! The head of his cock was inside my vagina. That is why it was still stretched. He pulled out completely before pushing back between my lips and into me. That first penetration by his cock alone was awesome. He pulled out and re-entered me again. This he did four times, triggering very intense sensations and desires within my pussy.

George repositioned me on the bed, propped me up slightly so that I could see my mound and his cock. He moved between my legs keeping his upper body propped up with his arms. His cock was rigid and wet. I felt its head push between my pussy lips yet again, but this time he didn't withdraw. With gentle rocking motions, he pushed it deeper and deeper into me. I could see its length disappear under my mound and I could feel it driving into me. George stopped when his full length was inside. It was not sore, but I was so stretched and full that I felt quite uncomfortable. Then, biology kicked in. More juices started to flow and my vagina readjusted itself to fit around and comfortably enclose his large cock.

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