I was fourteen when my parents took me to Italy for a holiday. Whilst there I became fascinated with the old Roman buildings and ruins. This encouraged me to take an interest in history and archaeology.When I left school, I went on to university to study both subjects.I was eighteen when I returned to Rome to renew my acquaintance with the ruins I had become fascinated with.Whilst there I visited Pompeii and there became even more fascinated with the history of that place.I returned home and continued my studies with my mind and interests refreshed and even more curious.I began to write a dissertation about Pompeii.A family friend I had known all my life was “Uncle” Tom. He often dropped in to chat with me about my fascination with Italy and the ruins I had begun to study. He is an Architect and had an interest in Roman architecture and was able to explain a lot of my questions that assisted me in my research.The term ‘Uncle’ was not entirely correct. He was single, aged in his 40’s, and a friend of my parents, rather than a relative. I had known him all my life. Not long after I turned eighteen, he suggested that I just call him Tom in future, something I had no problems doing.Tom is a lovely man and I treated him as a close friend and confidant. He was a man whose company everybody enjoyed. He visited us often and had a reputation as a lover boy. The women friends who accompanied him rarely lasted more than a couple of weeks.His life was not without a bit of scandal and my parents often joked about his love life. The stories of his romances and seductions were interesting and humorous. Many of the women he entertained were younger wives of some quite prominent older men.He always complimented me on my appearance, and I felt that it was just part of his charm. Never did he suggest anything inappropriate, but I knew if he did, I would be willing. Like most of his women friends, I found him charming. I was envious of his attention to other women.Whilst I was in Pompeii I obtained a DVD that had been produced for a TV programme and contained a lot of valuable information that I found more than interesting. I also visited many of the sites and museums that had relics and other items regarding the ruins and the volcanic eruption which decimated the town. On a subsequent visit, I went to a museum with a section that depicted the sexual nature of the population. It was very specific and had many casts of people considered to be engaged in some form of sexual performance when they died during the eruption. This museum was not one of the sites promoted for tourists but more for research.I invited Tom to come to my room regularly to discuss my research. I often had him peruse essays I had to prepare as part of my course. As a result, I already had many interesting discussions with him regarding Roman Architecture, both in Italy and in other places in Europe the Romans had occupied.I often watched a DVD film about Caligula – a Roman Emperor who had contracted Syphilis which had affected his mind. He was well known for his orgies and improper relationships with his sisters. One aspect of his sordid life was to attend weddings and take the bride’s virginity before buggering her husband. It was said he did that ‘because he could’ as emperor.I enjoyed the film and watched it many times as I enjoyed the debauchery of the time and wondered how true it was. I found many of the orgy scenes in the film extremely lifelike. To make the film I believe the actors that were used in the very vivid orgy scenes were Penthouse and Playboy models who were prepared to engage in full sex while making the film.I was a virgin and I masturbated often while watching the film. I enjoyed the erotica.One afternoon Tom came to my room while I was watching the film. I was not expecting him or anybody else, so I had not locked the door. He just entered without knocking, unlike my parents who always knocked.He was somewhat bemused to find me naked, masturbating and watching the film on a large TV screen. He made no effort to look away or appear embarrassed.He smiled and told me, “Sorry I have come at the wrong time. I will come back when you have finished and when you are more appropriately attired.”“No wait,” I told him.It was not the first time he had seen me naked. Our family often skinny-dipped in our pool. The fact I was masturbating and looking at a virtual porn movie didn’t bother him.I grabbed a gown I had been wearing before disrobing completely to enjoy my pleasures.I think the fact I was masturbating, and the orgy being displayed on the TV amused him. Neither of us seemed perturbed by the scene he witnessed.“That is a very interesting study subject,” he joked.After the initial confusion of finding me in the situation he discovered me in, we settled down to have Göztepe Escort a conversation regarding my research and writings. I told him I had read of Caligula and had watched the film a few times. He told me he had only heard of the film but had not seen it.I offered to restart the film so he could watch it, and this cleared the air a little. After a short discussion regarding the pornography in the film, I assured him I had watched the movie a few times and it did not bother me. It aroused me and I enjoyed masturbating while watching it.Without any concern, he asked me if I was sexually experienced.“Unfortunately, no. I am still a virgin. Caligula would have had great pleasure in deflowering me,” I joked.He was amused and told me he would also enjoy that pleasure if he had been Caligula.I smiled and said, “I hope you would be more considerate than Caligula.”We began to watch the film again. As the film progressed, we discussed various aspects of life and the times they enjoyed at that time. The orgies were blatantly sexual and arousing. Tom said nothing but I saw him look at me judging my reactions. It was very explicit and brutal at times. We both discussed whether it was a true depiction.Tom confirmed to me that the film director encouraged the actors to engage in full sex while being filmed, and they were following directions. The film I considered had enhanced several aspects of debauchery to make it more ‘appealing’ to the audience who would be prepared to watch such scenes.“I would have liked to have been there,” Tom said.“In real life or the film?”“Both.”I told him it would have been an interesting time to live as a woman.He told me, “Your virginity would have been well behind you then.”“Are you asking me if I would have lost it to Caligula?”“If hadn’t been him it might have been me.”“That would have been fun,” I quipped.I let the gown fall open as I was sitting in a chair a short distance from him. I was getting bolder.“I think both of us would have enjoyed it. Would you mind if I removed my clothing, we would both be more comfortable,” he asked.“It won’t bother me, I have seen you nude before,” I assured him.“Not like this,” he commented as he removed his clothing and exposed his rigid penis.I had seen him slack but had never seen him erect before.I was fascinated and suppressed my fascination but found it hard to take my eyes off it. In a way it was attractive. It had a slight curve up to the left and was about seven inches long and thick. The head of it was perfectly shaped and his balls hang low beneath it. It wiggled when he walked.“Oh God that is fascinating. It’s different to Caligula’s.” I would have loved to have touched it.“I have only seen my father like that once a year or so ago. I had seen him and mum by the pool having sex.” “Only this has been many places your father has never been.”“What are you trying to tell me?”“Jan, you know, and I know I am single and a woman to me is fair game. If she is interested, then I am more than interested.” “I have heard stories. I don’t think marriage is a barrier for you. Have you slept with my mother?”“No, but only out of respect for your father, believe me, if she wasn’t married to him, I would have had her by now.”“What about me? Would you consider taking me to your bed?”I had overstepped the boundary of common sense. The film aroused me, and I was being cheeky.He looked straight at me. “Jan, nothing would give me greater pleasure than to share your virginity with you. You are old enough to know your mind and make that decision for yourself.”“You are telling me that if I agreed, you would be willing to have sex with me?”“Yes, without hesitation. Particularly as you are still a virgin, I have not had that pleasure in my entire life. I would love to show you all the wonderful experiences you can enjoy with a man who knows how to treat a woman in the way women like to be treated.”“As you have treated many, I gather.”“Far too many to count. And with no complaints.”“And no pregnancies?”“None, that I am aware of. I am sure that if that was to have happened, I would have known by now.”“Tom, you are making a case for me to consider with a great deal of thought. I have often wondered who that man might be. I have had many offers to sleep with many of my boyfriends, but I made the decision not to until I believe I was old enough to recognise the right guy to get that prize.”“Jan it should be with a man before you marry and with a man you respect. You will remember that man and that event all your life. It is a big decision for a woman. Many girls do not realise how serious it is and far too many regret the fact it’s over before it began. They are unsatisfied and coerced into it more often than not.”“Are you telling me that you are the man for Göztepe Escort Bayan me? And I would not regret it if I were to sleep with you as that man who would forever be in my memory.”“Exactly. Think about it, we are here alone, and we could quite easily enjoy ourselves for the entire evening, doing something I will never regret or forget. I will ensure that you will feel the same afterwards. I promise.”“That is a tricky thing to promise a woman. How do you know I won’t regret it?”“That is something I have learned over time. I have never had a woman regret sleeping with me, only the fact she was being unfaithful to her husband, which many had done.”“You are telling me you have never had a woman unsatisfied or regretting what they had done with you?”“To the best of my knowledge. I have never had a complaint.”“You certainly have a way with words, and I have noticed that many times before. My father has been heard to say you could charm the pants off a statue.”“Thank you for the compliment.”“I have heard my mother reply, ‘mine too’.”Tom explained. “Your mother knows more than you might imagine, she is well aware of some of my conquests. I don’t have many secrets from her or your father.”“Then there will be one, or I am not interested. They must never know what we are going to do and what you have done with me.”“Am I to assume that you have made up your mind? There is no turning back the clock afterwards.”“No. It is a decision I have made. It is not an assumption.”My decision had not been instantaneous. I have considered it many times, but I have never considered it to be with a man as old as Tom. A skilled lover. His experience with older women is considerable. The more I thought about it the more convinced I had been I had made a good decision. I assumed he has not slept with a girl my age.“I am happy with that.”“I had never considered it would be with you believe me, but for some unaccountable reason, I have decided that is going to be you and here and now. I have made my decision and I am sure it is the right one. You will get your first virgin, and I will never regret the decision I have made.”I stood up and let the gown drop to the floor, I was now as naked as he was. He was standing there with his cock now slack and draped over his balls. I have seen many men like this. Mostly older men, as friends of our family. My parents are comfortable being naked around the pool in the company of friends. I think many just come for the experience.My limited experience with guys my age has been confined to a few boys, usually sons of friends of my parents who have been here. A kiss here and there and a bit of fumbling. Boys have not been a sexual attraction for me. I have always refused any sexual approaches as I have always wanted my first time to be with a guy I choose and not a fumble on the back seat of a car as many of my friends have described. A few of my girlfriends have had sex and we have talked about it and the boys they have done it with. Most had regrets.I attended an all-girls school and had little contact with boys my age except at a school formal where we were paired with guys our height. I have never seen a man with an erect penis in real life before seeing Tom, only on TV screens and in some porn magazines.I masturbate often and enjoy it.I had watched more than a few porn movies and the C movie numerous times in which there is explicit sexual coupling. I have never witnessed two people having sex in the flesh.Tom suggested we sit down and talk about what we had proposed.We talked about what I had told him. He wanted to confirm I knew what I was about to do and that I was happy that it was him with whom I was going to have sex. It was not lovemaking but purely sex. He had no interest in me as a lover ‘yet’ as he put it.“I am not planning on having a husband twice my age,” I assured him.“Nor me, a wife of any age,” he assured me.“Just to be sure, I am using contraception.”“There is no need to worry, I have had a vasectomy I can’t afford to take risks.”He then went on to tell me of a few experiences he has had with some of the women I knew as socialites, friends of the family, and a few who are not.“I can assure you none have been as young or as attractive as you are, you are beautiful. Particularly nude.”“Thank you. Do their husbands know?”“Not that I know of. None of their husbands has ever mentioned anything to me that gave me cause for concern.”“Do my parents know?”“Many of them have been guests here. You would have met a few.”“I gather my parents approve of you doing it here?”“Yes. They allow me to use your spare bedroom. Your father has told me to be careful, your mother has been more inquisitive.”“What will happen if I tell my mother I am no longer a virgin and who has had the Escort Göztepe pleasure of relieving me of it?” “I will be extremely pleased as I expect she will be. She and I have swapped notes on many occasions and have a clear understanding, I have never approached her for sex, as much as I would like to.”“Have you told her that?”“We have discussed it as she has been more than curious about one or two women. There is no doubt in either of our minds, her answer will always be ’no’.”“Then you will have to settle for second best,” I quipped.“That remains to be seen.”I was more than convinced that I had made a good decision.“I think the time for talking is over and it’s time when actions speak louder than words,” I told him.I went to my bed which is a big queen-sized bed and pulled the covers down. He helped me.“Tell me, what do you feel is the best way to begin?” I asked.“Missionary is the most popular way and that way we get to see each other’s expression as we enjoy the pleasure of each other’s bodies.”“I will be guided by you. Your experience is somewhat more extensive than mine.”“You will be the youngest woman I have had sex with within my memory, apart from my early days.”“How old were you when you have your first fuck?”“Sixteen.”“How old was she?” “She was with the mother of one of my friends. I guess between thirty and forty. I went over to my friend Dave’s place for a swim. He wasn’t home but his mother was. She was out by the pool topless, and I could not take my eyes off her breasts, and she began to prick-tease me. I got hard and it showed in my swimmers.”“That would be hard to hide,” I said as I looked at his hard cock.“She saw it and I was embarrassed.”“’Oh, you are a big boy,’ she said and then she came to me and kissed me. I was dumbfounded. As she kissed me, she slipped my swimmers down and exposed my cock. She bent down and kissed it and then said, ’fuck me.’ She had not realised I had never fucked anybody before.“Things happened so quickly and before I knew it, I was on top of her, and I was fucking her. It was hard for me to keep my cock inside her.“After a minute or two she told me to get up off her. I was confused and disappointed, but she then pushed me down and got on top of me and she began to fuck me.“She bounced about on top of me, and I came after a couple of minutes, I just did it inside her. Then she wriggled about on top of me still and she came too. I had never seen or heard a woman cum before and she was amazing.“After it was over she asked me if I liked fucking Dave’s mum.“I told her ‘It was fantastic. I haven’t fucked anybody before.'”‘That is amazing. Let us make it something special then.’ She was really surprised.“She told me that she liked doing it one way especially. Then showed me how to do it in doggy fashion.”“I think I know what you mean. I have seen them doing this in the movie.”“We can save that for another time,” he suggested.“Did you do it with her again?”“I went over when I knew Dave would be out, hoping she might do it again with me.”The minute I arrived she knew exactly what I was there for, and she told me, “This is the last time.”After we fucked, she told me that I hoped I would remember her. I will never forget her.“Did Dave ever find out?”“Not that I am aware of.”…..I looked at Tom and saw a mature man with a firm body and an erect penis. He was old enough to be my father. He was about to have sex with me for the first time. I felt comfortable with the decision I had made. He had not coerced me or tried to convince me that having sex with him would be anything but enjoyable. I was not nervous or worried about what we were about to do. I was calm and relaxed, I had thought about this hundreds of times but never imagined it would be as casual and as relaxed as it was, nor with a man his age. I just imagined I was one of the women in the movie.The only difference was it was to be my first experience of sex with a man. My virginity.By now I was quite wet thinking of what I was about to do. To Tom, it was just another conquest, but to me, it was an event of my life. We had talked for an hour, and now I wanted it more than I could ever remember. I was thinking of Caligula and how he treated the brides. I had no wish to be treated like he had treated them. I wanted this to be the highlight of my life until the day I get married.I looked at Tom standing there. He smiled at me which reassured me he was the right man to do as I wished. His cock was now rigid and sticking out with his balls dangling below it. I have seen many cocks when my parent’s friends have been here skinny-dipping. I have always taken them for granted as being part of a man. Many look different but I had never taken much notice of what a cock looks like in detail, now I was obsessed with what Tom’s looked like.I went to him and asked, “Can I touch it?”“Be my guest.”I then felt it, before studying it. It was warm and I was fascinated by the feel of its firmness in my hand. The skin had a nice smooth silky feeling and I stroked it a couple of times. I was surprised at how easily the skin slid up and down.